Pyridine and pyrazine compounds

ABSTRACT

The present invention relates to compounds of formula I 
     
       
         
         
             
             
         
       
     
     wherein the variables are defined as given in the description and claims. The invention further relates to uses and composition for compounds of formula I.

The present invention relates to pyridine and pyrazine compounds and theN-oxides and the salts thereof for combating phytopathogenic fungi, andto the use and methods for combating phytopathogenic fungi and to seedscoated with at least one such compound. The invention also relates toprocesses for preparing these compounds, intermediates, processes forpreparing such intermediates, and to compositions comprising at leastone compound I.

In many cases, in particular at low application rates, the fungicidalactivity of the known fungicidal compounds is unsatisfactory. Based onthis, it was an object of the present invention to provide compoundshaving improved activity and/or a broader activity spectrum againstphytopathogenic harmful fungi.

Surprisingly, this object is achieved by the use of the inventivepyridine compounds of formula I having favorable fungicidal activityagainst phytopathogenic fungi.

Accordingly, the present invention relates to the compounds of formula Icompounds of the formula I

-   -   wherein

-   R¹ is in each case independently selected from halogen, OH, NO₂, SH,    NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C₂-C₄-alkenyl),    N(C₂-C₄-alkenyl)₂, NH(C₂-C₄-alkynyl), N(C₂-C₄-alkynyl)₂,    NH(C₃-C₆-cycloalkyl), N(C₃-C₆-cycloalkyl)₂,    N(C₁-C₄-alkyl)(C₂-C₄-alkenyl), N(C₁-C₄-alkyl)(C₂-C₄-alkynyl),    N(C₁-C₄-alkyl)(C₃-C₆-cycloalkyl), N(C₂-C₄-alkenyl)(C₂-C₄-alkynyl),    N(C₂-C₄-alkenyl)(C₃-C₆-cycloalkyl),    N(C₂-C₄-alkynyl)(C₃-C₆-cycloalkyl), NH(C(═O)C₁-C₄-alkyl),    N(C(═O)C₁-C₄-alkyl), NH—SO₂—R^(x), S(O)_(m)—C₁-C₆-alkyl,    S(O)_(m)-aryl, C₁-C₆-cycloalkylthio, S(O)_(m)—C₂-C₆-alkenyl,    S(O)_(m)—C₂-C₆-alkynyl, CH(═O), C(═O)C₁-C₆-alkyl,    C(═O)C₂-C₆-alkenyl, C(═O)C₂-C₆-alkynyl, C(═O)C₃-C₆-cycloalkyl,    C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂, C(═O)N(C₂-C₆-alkenyl)₂,    C(═O)N(C₂-C₆-alkynyl)₂, C(═O)N(C₃-C₇-cycloalkyl)₂, CH(═S),    C(═S)C₁-C₆-alkyl, C(═S)C₂-C₆-alkenyl, C(═S)C₂-C₆-alkynyl,    C(═S)C₃-C₆-cycloalkyl, C(═S)O(C₂-C₆-alkenyl), C(═S)O(C₂-C₆-alkynyl),    C(═S)O(C₃-C₇-cycloalkyl), C(═S)NH(C₁-C₆-alkyl),    C(═S)NH(C₂-C₆-alkenyl), C(═S)NH(C₂-C₆-alkynyl),    C(═S)NH(C₃-C₇-cycloalkyl), C(═S)N(C₁-C₆-alkyl)₂,    C(═S)N(C₂-C₆-alkenyl)₂, C(═S)N(C₂-C₆-alkynyl)₂,    C(═S)N(C₃-C₇-cycloalkyl), C₁-C₆-alkyl, C₁-C₆-halogenalkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, OR^(Y), C₃-C₆-cycloalkyl, five- or    six-membered heteroaryl and aryl; wherein the heteroaryl contains    one, two or three heteroatoms selected from N, O and S; wherein

-   R^(x) is C₁-C₄-alkyl, C₁-C₄-halogenalkyl, unsubstituted aryl or aryl    that is substituted by 1, 2, 3, 4 or 5 substituents R^(x1)    independently selected from C₁-C₄-alkyl, halogen, OH, CN,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;

-   R^(Y) is C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,    C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, phenyl and    phenyl-C₁-C₆-alkyl; wherein the phenyl groups are unsubstituted or    carry one, two, three, four or five substituents selected from the    group consisting of CN, halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    wherein the acyclic moieties of R¹ are unsubstituted or substituted    by groups Ra which independently of one another are selected from:

-   R^(1a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio and    phenoxy, wherein the phenyl group is unsubstituted or substituted by    substituents R^(11a) selected from the group consisting of halogen,    OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and    C₁-C₄-halogenalkoxy;    wherein the carbocyclic, heteroaryl and aryl moieties of R¹ are    unsubstituted or substituted by groups R^(1b) which independently of    one another are selected from:

-   R^(1b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio;    -   and wherein m is 0, 1 and 2;

-   R² is in each case independently selected from halogen, OH, NO₂, SH,    NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C₂-C₄-alkenyl),    N(C₂-C₄-alkenyl)₂, NH(C₂-C₄-alkynyl), N(C₂-C₄-alkynyl)₂,    NH(C₃-C₆-cycloalkyl), N(C₃-C₆-cycloalkyl)₂,    N(C₁-C₄-alkyl)(C₂-C₄-alkenyl), N(C₁-C₄-alkyl)(C₂-C₄-alkynyl),    N(C₁-C₄-alkyl)(C₃-C₆-cycloalkyl), N(C₂-C₄-alkenyl)(C₂-C₄-alkynyl),    N(C₂-C₄-alkenyl)(C₃-C₆-cycloalkyl),    N(C₂-C₄-alkynyl)(C₃-C₆-cycloalkyl), NH(C(═O)C₁-C₄-alkyl),    N(C(═O)C₁-C₄-alkyl), NH—SO₂—R^(x), S(O)_(m)—C₁-C₆-alkyl,    S(O)_(m)-aryl, C₁-C₆-cycloalkylthio, S(O)_(m)—C₂-C₆-alkenyl,    S(O)_(m)—C₂-C₆-alkynyl, CH(═O), C(═O)C₁-C₆-alkyl,    C(═O)C₂-C₆-alkenyl, C(═O)C₂-C₆-alkynyl, C(═O)C₃-C₆-cycloalkyl,    C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂, C(═O)N(C₂-C₆-alkenyl),    C(═O)N(C₂-C₆-alkynyl), C(═O)N(C₃-C₇-cycloalkyl), CH(═S),    C(═S)C₁-C₆-alkyl, C(═S)C₂-C₆-alkenyl, C(═S)C₂-C₆-alkynyl,    C(═S)C₃-C₆-cycloalkyl, C(═S)O(C₂-C₆-alkenyl), C(═S)O(C₂-C₆-alkynyl),    C(═S)O(C₃-C₇-cycloalkyl), C(═S)NH(C₁-C₆-alkyl),    C(═S)NH(C₂-C₆-alkenyl), C(═S)NH(C₂-C₆-alkynyl),    C(═S)NH(C₃-C₇-cycloalkyl), C(═S)N(C₁-C₆-alkyl)₂,    C(═S)N(C₂-C₆-alkenyl), C(═S)N(C₂-C₆-alkynyl),    C(═S)N(C₃-C₇-cycloalkyl), C₁-C₆-alkyl, C₁-C₆-halogenalkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, OR^(Y), C₃-C₆-cycloalkyl, five- or    six-membered heteroaryl and aryl; wherein the heteroaryl contains    one, two or three heteroatoms selected from N, O and S; wherein

-   R^(x) is defined as above;

-   R^(Y) is defined as above;    wherein the acyclic moieties of R² are unsubstituted or substituted    by groups R^(2a) which independently of one another are selected    from:

-   R^(2a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio and    phenoxy, wherein the phenyl group is unsubstituted or substituted by    substituents R^(21a) selected from the group consisting of halogen,    OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and    C₁-C₄-halogenalkoxy;    wherein the carbocyclic, heteroaryl and aryl moieties of R² are    unsubstituted or substituted by groups R^(2b) which independently of    one another are selected from:

-   R^(2b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio; and

-   U is N or CR³;

-   R³ is selected from H, halogen, OH, CN, NO₂, SH, NH₂,    NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, five-    or six-membered heteroaryl and aryl; wherein the heteroaryl contains    one, two or three heteroatoms selected from N, O and S; wherein

-   R^(x) is defined as above;    and wherein the aliphatic moieties of R³ are unsubstituted or    substituted with identical or different groups R^(3a) which    independently of one another are selected from:

-   R^(3a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl    and phenoxy, wherein the aryl and phenoxy group is unsubstituted or    carries 1, 2, 3, 4 or 5 substituents R^(31a) selected from the group    consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    and wherein the cycloalkyl, heteroaryl and aryl moieties of R³ are    unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximum    number of identical or different groups R^(3b) which independently    of one another are selected from:

-   R^(3b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio;

-   R⁴ is selected from H, halogen, OH, CN, NO₂, SH, NH₂,    NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, five-    or six-membered heteroaryl and aryl; wherein the heteroaryl contains    one, two or three heteroatoms selected from N, O and S; wherein

-   R^(x) is defined as above;    -   and wherein the aliphatic moieties of R⁴ are unsubstituted or        substituted with identical or different groups R^(4a) which        independently of one another are selected from:

-   R^(4a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl    and phenoxy, wherein the aryl and phenoxy group is unsubstituted or    carries 1, 2, 3, 4 or 5 substituents R^(41a) selected from the group    consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    and wherein the cycloalkyl, heteroaryl and aryl moieties of R⁴ are    unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximum    number of identical or different groups R⁴ which independently of    one another are selected from:

-   R^(4b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio;

-   Y is O or S(O)_(m), wherein

-   m is defined as above;

-   Z is N or CR⁵;

-   R⁵ is independently selected from H, halogen, OH, CN, NO₂, SH, NH₂,    NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),    N(C(═O)C₁-C₄-alkyl), NH—SO₂—R^(x), CH(═O), C(═O)C₁-C₆-alkyl,    C(═O)NH(C₁-C₆-alkyl), CR′═NOR″, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,    C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkenyl, S(O)_(m)—C₁-C₆-alkyl, three-, four-, five- or    six-membered saturated or partially unsaturated heterocycle, five-    or six-membered heteroaryl and phenyl; wherein the heterocycle or    heteroaryl contains one, two or three heteroatoms selected from N, O    and S; and wherein R′ and R″ are independently unsubstituted or    substituted by R′″ which is independently selected from halogen, OH,    CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x),    C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,    C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl,    C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl and phenyl; wherein m and R^(x) is as    defined above;    and wherein the aliphatic moieties of R⁵ are not further substituted    or carry 1, 2, 3 or up to the maximum possible number of identical    or different groups R^(5a) which independently of one another are    selected from:

-   R^(5a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,    C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    five- or six-membered heteroaryl, phenyl and phenoxy, wherein the    heteroaryl, phenyl and phenoxy group is unsubstituted or    unsubstituted or substituted with R^(51a) selected from the group    consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    wherein the alicyclic, phenyl, heterocyclic and heteroaryl moieties    of R⁵ are unsubstituted or substituted with identical or different    groups R^(5b) which independently of one another are selected from:

-   R^(5b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy, and C₁-C₆-alkylthio;

-   X is independently selected from halogen, OH, CN, NO₂, SH,    NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),    N(C(═O)C₁-C₄-alkyl), NH—SO₂—R^(x), CH(═O), C(═O)C₁-C₆-alkyl,    C(═O)NH(C₁-C₆-alkyl), CR′═NOR″, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,    C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkenyl, S(O)_(m)—C₁-C₆-alkyl, three-, four-, five- or    six-membered saturated or partially unsaturated heterocycle, five-    or six-membered heteroaryl and phenyl; wherein the heterocycle or    heteroaryl contains one, two or three heteroatoms selected from N, O    and S; wherein m, R′, R″ and R is as defined above;    and wherein the aliphatic moieties of X are not further substituted    or carry 1, 2, 3 or up to the maximum possible number of identical    or different groups X^(a) which independently of one another are    selected from:

-   X^(a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,    C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    five- or six-membered heteroaryl, phenyl and phenoxy, wherein the    heteroaryl, phenyl and phenoxy group is unsubstituted or    unsubstituted or substituted with X^(1a) selected from the group    consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    wherein the alicyclic, phenyl, heterocyclic and heteroaryl moieties    of X are unsubstituted or substituted with identical or different    groups X^(b) which independently of one another are selected from:

-   X^(b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy, and C₁-C₆-alkylthio;

-   n is 0, 1, or 2;

-   Q¹ is selected from CN, halogen, —C₁-C₆-alkyl, C₁-C₆-halogenalkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, three-, four-, five-    or six-membered saturated or partially unsaturated heterocycle,    five- or six-membered heteroaryl and aryl; wherein the heterocycle    and heteroaryl contains one, two or three heteroatoms selected from    N, O and S;    wherein the aliphatic moieties of Q¹ are unsubstituted or    substituted with identical or different groups Q^(1a) which    independently of one another are selected from:

-   Q^(1a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    phenyl and phenoxy, wherein the phenyl and phenoxy group is    unsubstituted or carries 1, 2, 3, 4 or 5 substituents Q^(1a)    selected from the group consisting of halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    wherein the cycloalkyl, heterocyclic, heteroaryl and aryl moieties    of Q¹ are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to    the maximum number of identical or different groups Q^(b) which    independently of one another are selected from:

-   Q^(1b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio;

-   Q² is selected from H, halogen, —C₁-C₆-alkyl, C₁-C₆-halogenalkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, three-, four-, five-    or six-membered saturated or partially unsaturated heterocycle,    five- or six-membered heteroaryl and aryl; wherein the heterocycle    and heteroaryl contains one, two or three heteroatoms selected from    N, O and S;    wherein the aliphatic moieties of Q² are unsubstituted or    substituted with identical or different groups Q^(2a) which    independently of one another are selected from:

-   Q^(2a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    phenyl and phenoxy, wherein the phenyl and phenoxy group is    unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q¹²    selected from the group consisting of halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;

-   wherein the cycloalkyl, heterocyclic, heteroaryl and aryl moieties    of Q² are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to    the maximum number of identical or different groups Q^(2b) which    independently of one another are selected from: Q^(2b) halogen, OH,    CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio;    Q¹ and Q² together with the carbon atom to which they are bound form    a three- to seven-membered saturated or partially unsaturated    carbo-, or heterocycle    wherein the ring may further contain 1, 2, 3 or 4 heteroatoms    selected from N—R^(N), O and S, wherein R^(N) is selected from H,    C₁-C₄-alkyl and SO₂R^(Q); wherein

-   R^(Q) is selected from C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    unsubstituted aryl or heteroaryl that is substituted by 1, 2, 3, 4    or 5 substituents R^(Q1) independently selected from C₁-C₄-alkyl;    and wherein S may be in the form of its oxide SO or SO₂; and wherein    in each case one or two CH₂ groups of the carbo- or heterocycle may    be replaced by a group independently selected from C(═O) and C(═S);    and wherein the ring is unsubstituted or substituted with 1, 2, 3,    4, 5 or up to the maximum number of identical or different groups    R^(QR) which independently of one another are selected from:    Q^(R) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio;

-   W is O, S(O)_(m) or NQ⁴

-   m is defined as above;

-   Q³ is selected from substituted C₁-C₁₅-alkyl, C₁-C₁₅-halogenalkyl,    C₂-C₁₅-alkenyl, C₂-C₁₅-halogenalkenyl, C₂-C₁₅-alkynyl,    C₃-C₇-cycloalkyl, S(O)_(m)—C₁-C₁₅-alkyl, S(O)_(m)—C₁-C₁₅-alkoxy,    S(O)_(m)-aryl, S(O)_(m)—C₂-C₁₅-alkenyl, S(O)_(m)—C₂-C₁₅-alkynyl,    C(═O)C₁-C₁₅-alkyl, C(═O)C₁-C₁₅-halogenalkyl, C(═O)C₂-C₁₅-alkenyl,    C(═O)C₂-C₁₅-alkynyl, C(═O)C₃-C₇-cycloalkyl, C(═O)aryl,    C(═O)NH(C₁-C₁₅-alkyl), C(═O)N(C₁-C₁₅-alkyl)₂,    C(═O)NH(C₂-C₁₅-alkenyl), C(═O)N(₂—C₁₅-alkenyl),    C(═O)NH(C₂-C₁₅-alkynyl), C(═O)N(C₂-C₁₅-alkynyl),    C(═O)NH(C₃-C₇-cycloalkyl), C(═O)N(C₃-C₇-cycloalkyl),    C(═S)C₁-C₁₅-alkyl, C(═S)C₂-C₁₅-alkenyl, C(═S)C₂-C₁₅-alkynyl,    C(═S)C₃-C₆-cycloalkyl, C(═S)aryl, C(═S)O(C₁-C₁₅-alkyl),    C(═S)O(C₂-C₁₅-alkenyl), C(═S)O(C₂-C₁₅-alkynyl),    C(═S)O(C₃-C₇-cycloalkyl), C(═S)NH(C₁-C₁₅-alkyl),    C(═S)NH(C₂-C₁₅-alkenyl), C(═S)NH(C₂-C₁₅-alkynyl),    C(═S)NH(C₃-C₇-cycloalkyl), C(═S)N(C₁-C₁₅-alkyl)₂,    C(═S)N(C₂-C₁₅-alkenyl), C(═S)N(C₂-C₁₅-alkynyl),    C(═S)N(C₃-C₇-cycloalkyl)₂, C₃-C₆-cycloalkyl, three-, four-, five- or    six-membered saturated or partially unsaturated heterocycle, five-    or six-membered heteroaryl, and aryl; wherein the heterocycle and    heteroaryl contains one, two or three heteroatoms selected from N, O    and S; wherein in each case one or two CH₂ groups of the carbocycle    and heterocycle may be replaced by a group independently selected    from C(═O) and C(═S)    wherein the aliphatic moieties of Q³ except for substituted    C₁-C₁₅-alkyl moieties are unsubstituted or substituted with    identical or different groups Q^(3a) which independently of one    another are selected from:

-   Q^(3a) halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),    N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,    NH—SO₂—R^(x), C₁-C₆-halogenalkylthio, S(O)_(m)—C₁-C₆-alkyl,    S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl, CH(═O),    C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),    C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, C₁-C₆-alkoxy C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    phenyl, phenoxy and five- to ten-membered heterocycle, heteroaryl,    heterocycloxy and heteryloxy; wherein in each case one or two CH₂    groups of the carbocycle and heterocycle may be replaced by a group    independently selected from C(═O) and C(═S); wherein the heterocycle    or heteroaryl contains one, two or three heteroatoms selected from    N, O and S; wherein the carbocyclic, heterocyclic, aryl, phenoxy,    and heteroaryl groups are unsubstituted or substituted with 1, 2, 3,    4 or 5 substituents Q^(3a) selected from the group consisting of    halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,    NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x),    C₁-C₆-alkylthio, S(O)_(m)—C₁-C₆-alkyl, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, CR′═NOR″,    phenyl, phenoxy and five- to ten-membered heterocycle and    heteroaryl; wherein the heterocycle or heteroaryl contains one, two    or three heteroatoms selected from N, O and S; and wherein the    phenyl, phenoxy, heterocycle and heteroaryl groups are unsubstituted    or substituted with 1, 2, 3, 4 or 5 substituents Q^(31a) selected    from the group consisting of halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, CN, CR′═NOR″ and    C₁-C₄-halogenalkoxy; and wherein m, R^(x), R′ and R″ is defined as    above;    wherein the carbocycle, heterocycle, heteroaryl and aryl moieties of    Q³ are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the    maximum number of identical or different groups Q^(3b) which    independently of one another are selected from:

-   Q^(3b) halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),    N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,    NH—SO₂—R^(x) C₁-C₄-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    S(O)_(m)—C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, phenoxy and    five- to ten-membered heterocycle, heteroaryl, heterocycloxy,    heteryloxy; wherein the heterocycle or heteroaryl contains one, two    or three heteroatoms selected from N, O and S; wherein the phenyl,    phenoxy, heterocycle and heteroaryl groups are unsubstituted or    substituted with 1, 2, 3, 4 or 5 substituents Q^(31b) selected from    the group consisting of halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, CR′═NOR″;    phenyl, phenoxy and five- to ten-membered heterocycle and    heteroaryl; wherein the heterocycle or heteroaryl contains one, two    or three heteroatoms selected from N, O and S; and wherein the    phenyl, phenoxy, heterocycle and heteroaryl groups are unsubstituted    or substituted with 1, 2, 3, 4 or 5 substituents Q^(311b) selected    from the group consisting of halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, CN, CR′═NOR″ and    C₁-C₄-halogenalkoxy; and wherein R′ and R″ are defined as above;    wherein the substituted C₁-C₁₅-alkyl moieties of Q³ carry one, two,    three or up to the maximum possible number of identical or different    groups Q^(3c), respectively, which independently of one another are    selected from:

-   Q^(3c) halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),    N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,    NH—SO₂—R^(x), C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,    C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio,    S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl,    CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),    C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, a saturated or partially unsaturated    three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered    carbocycle or heterocycle, aryl and five-, six- or ten-membered    heteroaryl, heterocycloxy, heteryloxy; wherein in each case one or    two CH₂ groups of the carbocycle and heterocycle may be replaced by    a group independently selected from C(═O) and C(═S); wherein the    heterocycle and heteroaryl contain independently one, two, three or    four heteroatoms selected from N, O and S; wherein the carbocyclic,    heterocyclic, aryl, phenoxy and heteroaryl groups are independently    unsubstituted or carry one, two, three, four or five substituents    Q³¹ selected from the group consisting of s halogen, OH, CN, NO₂,    SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),    N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,    S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″; phenyl, phenoxy and five- to    ten-membered heterocycle and heteroaryl; wherein the heterocycle or    heteroaryl contains one, two or three heteroatoms selected from N, O    and S; and wherein the phenyl, phenoxy, heterocycle and heteroaryl    groups are unsubstituted or substituted with 1, 2, 3, 4 or 5    substituents Q^(311c) selected from the group consisting of halogen,    OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, CN, CR′═NOR″ and    C₁-C₄-halogenalkoxy; and wherein R′ and R″ is defined as above;    wherein m, R^(x), R′ and R″ is as defined above;

-   Q⁴ is selected from hydrogen, OH, CH(═O), C(═O)C₁-C₆-alkyl,    C(═O)C₂-C₆-alkenyl, C(═O)C₂-C₆-alkynyl, C(═O)C₃-C₆-cycloalkyl,    C(═O)O(C₁-C₆-alkyl), C(═O)O(C₂-C₆-alkenyl), C(═O)O(C₂-C₆-alkynyl),    C(═O)O(C₃-C₆-cycloalkyl), C(═O)NH(C₁-C₆-alkyl),    C(═O)NH(C₂-C₆-alkenyl), C(═O)NH(C₂-C₆-alkynyl),    C(═O)NH(C₃-C₆-cycloalkyl), C(═O)N(C₁-C₆-alkyl)₂,    C(═O)N(C₂-C₆-alkenyl), C(═O)N(C₂-C₆-alkynyl),    C(═O)N(C₃-C₆-cycloalkyl), CH(═S), C(═S)C₁-C₆-alkyl,    C(═S)C₂-C₆-alkenyl, C(═S)C₂-C₆-alkynyl, C(═S)C₃-C₆-cycloalkyl,    C(═S)O(C₁-C₆-alkyl), C(═S)O(C₂-C₆-alkenyl), C(═S)O(C₂-C₆-alkynyl),    C(═S)O(C₃-C₆-cycloalkyl), C(═S)NH(C₁-C₆-alkyl),    C(═S)NH(C₂-C₆-alkenyl), C(═S)NH(C₂-C₆-alkynyl),    C(═S)NH(C₃-C₆-cycloalkyl), C(═S)N(C₁-C₆-alkyl)₂,    C(═S)N(C₂-C₆-alkenyl), C(═S)N(C₂-C₆-alkynyl),    C(═S)N(C₃-C₆-cycloalkyl)₂, C₁-C₆-alkyl, C₁-C₄-halogenalkyl,    C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkoxy, OR^(Y), C₁-C₆-alkylthio,    C₁-C₆-halogenalkylthio, C₂-C₆-alkenyl, C₂-C₆-halogenalkenyl    C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl, S(O)_(m)—C₁-C₆-alkyl,    S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)—C₁-C₆-alkoxy,    S(O)_(m)—C₂-C₆-alkenyl, S(O)_(m)—C₂-C₆-alkynyl, S(O)_(m)aryl,    SO₂—NH(C₁-C₆-alkyl), SO₂—NH(C₁-C₆-halogenalkyl), SO₂—NH-aryl,    tri-(C₁-C₆ alkyl)silyl and di-(C₁-C₆ alkoxy)phosphoryl), five- or    six-membered heteroaryl and aryl; wherein the heteroaryl contains    one, two or three heteroatoms selected from N, O and S; wherein the    aryl groups are unsubstituted or carry one, two, three, four or five    substituents selected from the group consisting of CN, halogen, OH,    C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and    C₁-C₄-halogenalkoxy;

-   R^(Y) is defined as above;    -   wherein the acyclic moieties of Q⁴ are not further substituted        or carry one, two, three or up to the maximum possible number of        identical or different groups Q which independently of one        another are selected from:    -   Q^(4a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,        C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,        five- or six-membered heteroaryl, phenyl and phenoxy, wherein        the heteroaryl, phenyl and phenoxy group is unsubstituted or        carries one, two, three, four or five substituents Q^(4a)        selected from the group consisting of halogen, OH, C₁-C₄-alkyl,        C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;        -   wherein the alicyclic, phenyl, heterocyclic and heteroaryl            moieties of Q⁴ are not further substituted or carry one,            two, three, four, five or up to the maximum number of            identical or different groups Q^(4b) which independently of            one another are selected from:    -   Q^(4b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,        C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio;    -   and wherein m is defined as above;

-   with the proviso that if

-   U is CR³

-   W cannot be O or S(O)_(m)    and of an agriculturally acceptable salt thereof. and of the    compositions for combating phytopathogenic fungi.

The numbering of the ring members in the compounds of the presentinvention is as given in formula I above:

Compounds of type I can be prepared by reacting compounds of type IIwith a suitable electrophile Q³-LG in an organic solvent, preferably NMPor a halocarbon and in the presence of a base at temperatures between−20 and 100° C., most preferably between 0 and 40° C. LG represents asuitable leaving group, preferably a halogen or a sulfonate.

Alternatively compounds I may be obtained by reacting compounds II* withcompounds Q3-W—H under conditions described for the reaction betweencompounds and Q3-LG yielding compounds I.

Compounds of type I-1 can also be obtained by reacting compounds II**with compounds Q3*-CN under conditions described for the reactionbetween compounds II and Q3-LG yielding compounds I-I

Compounds of type I-2 can be obtained via reaction with a reactive groupQ⁴-LG. Reactive groups are preferably C₁-C₈-alkyl halides, C₂-C₆-alkenylhalides, C₂-C₆-alkynyl halides, benzyl halides, aldehydes, ester, acidchlorides, amides, sulfates, silyl halides or phosphates, e.g.carboxylic acid (LG=OH), aldehydes (LG=H), acid chloride (LG=Cl), amides(LG=NMe₂) or phosphates (LH=OCH₃).

Typically the reaction is performed in a range between 0° C. and ambienttemperature in the presence of a reactive group and organic base.Suitable base preferably NEt₃, pyridine NaOH, TEBAC, K₂CO₃, NaCO₃ orKOH. Most preferably solvents are THF, DMF, DMSO, MeOH or water (see forexample, Journal of Medicinal Chemistry, 1989, 32(6), 1242-1248;European Journal of Medicinal Chemistry, 2009, 44(10), 4034-4043).

Compounds of type II may be accessed as described for example inJP2010/202530 or Angewandte Chemie, International Edition, 45(35),5803-5807; 2006 and as outlined below. Compounds of type III (where Halis a halogen, most preferably Br or I) can be metallated by treatmentwith an appropriate organometallic reagent [M] in an ethereal solvent atlow temperatures. Preferably, an organolithium or organomagnesiumcompound is used and the reaction is best performed in THF and between−78° C. and 0° C. The intermediary organometallic species can be trappedwith carbonyl, thiocarbonyl or imines compounds of type IV to furnishcompounds of type II after aqueous workup. Compounds of type IV arereadily available either from commercial suppliers or through methodsobvious to a person skilled in the art.

To access compounds of type III, it may be preferred to react compoundsV in a nucleophilic aromatic substitution with compounds of type VIwhich are either commercially available or can be prepared followingprocedures that are obvious to a skilled person. LG represents asuitable leaving group, with special preference given to fluoride (forprecedents see e.g. WO2007/117381, WO2012/037782, or Bioorganic &Medicinal Chemistry, 21(4), 979-992; 2013). The reaction is best carriedout at temperatures between 0 and 100° C., preferably between roomtemperature and 80° C. Furthermore, it may be appropriate to perform thereaction in an organic solvent, preferably, but not limited to DMF orNMP and in the presence of a base, preferably, but not limited topotassium carbonate or sodium hydride.

Alternatively compounds III can be synthesized reacting compounds V* andVI* applying conditions already described for the reaction of compoundsV with compounds VI

Alternatively compounds III* can be accessed by reacting compounds V*with compounds VI** applying conditions already described for thereaction of V* with VI* yielding compounds III*. Compounds III* cansubsequently be converted to compounds II using methods alreadydescribed for the reaction of compounds III with compounds IV yieldingcompounds II

Additionally compounds III* can be accessed by reacting compounds V withcompounds V*** applying conditions already described for the reaction ofV* with VI* yielding compounds III*.

Compounds of type V can be prepared from nitro compounds of type VII ina two-step sequence that has been previously described (for examples seeJournal of Medicinal Chemistry, 35(20), 3667-71; 1992, WO2005/123668, orUS20060293364). The first step seeks to achieve a chemoselectivereduction of the nitro group to its amino congener by employing asuitable reducing agent, such as iron, zinc, or hydrogen in the presenceof a transition metal catalyst such as palladium. Preferably, thereduction is performed in an organic solvent, more preferably in analcoholic solvent, if appropriate at elevated temperatures and/orincreased pressure. The respective amino compounds can be transformedinto compounds of type V through a Sandmeyer reaction by reacting themfirst with a suitable nitrite source at low temperatures, preferably butnot limited to sodium nitrite or t-BuONO. For the preparation ofcompounds in which Y is oxygen, the intermediary diazonium salt may betreated with a suitable acid, for example, but not limited to HCl orHBF₄. It may be appropriate to increase the temperature upon addition ofthe acid. Compounds in which Y is S can be accessed by reacting saiddiazonium salt with a suitable sulfur source, preferably a alkalixanthate such as potassium xanthate, followed by base-mediated cleavageof the thioester. A precedent can be found for example in Journal ofMedicinal Chemistry, 36(8), 953-66; 1993.

A person skilled in the art will realize that compounds of type VII areeither commercially available or be able to prepare said compoundsfollowing standard procedures.

The N-oxides may be prepared from the inventive compounds according toconventional oxidation methods, e. g. by treating compounds I with anorganic peracid such as metachloroperbenzoic acid (cf. WO 03/64572 or J.Med. Chem. 38(11), 1892-903, 1995); or with inorganic oxidizing agentssuch as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981)or oxone (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001). The oxidationmay lead to pure mono-N-oxides or to a mixture of different N-oxides,which can be separated by conventional methods such as chromatography.

In the following, the intermediate compounds are further described. Askilled person will readily understand that the preferences for thesubstituents, also in particular the ones given in the tables below forthe respective substituents, given herein in connection with compounds Iapply for the intermediates accordingly. Thereby, the substituents ineach case have independently of each other or more preferably incombination the meanings as defined herein.

If the synthesis yields mixtures of isomers, a separation is generallynot necessarily required since in some cases the individual isomers canbe interconverted during work-up for use or during application (e. g.under the action of light, acids or bases). Such conversions may alsotake place after use, e. g. in the treatment of plants in the treatedplant, or in the harmful fungus to be controlled.

In the definitions of the variables given above, collective terms areused which are generally representative for the substituents inquestion. The term “C_(n)-C_(m)” indicates the number of carbon atomspossible in each case in the substituent or substituent moiety inquestion.

The term “halogen” refers to fluorine, chlorine, bromine and iodine.

The term “C₁-C₆-alkyl” refers to a straight-chained or branchedsaturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl,ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-2-methylpropyl. Likewise, the term “C₂-C₄-alkyl” refers to astraight-chained or branched alkyl group having 2 to 4 carbon atoms,such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propoyl), butyl,1-methylpropyl (sec.-butyl), 2-methylpropyl (iso-butyl),1,1-dimethylethyl (tert.-butyl).

The term “C₁-C₆-halogenalkyl” refers to an alkyl group having 1 or 6carbon atoms as defined above, wherein some or all of the hydrogen atomsin these groups may be replaced by halogen atoms as mentioned above.Examples are “C₁-C₂-halogenalkyl” groups such as chloromethyl,bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.

The term “C₁-C₆-hydroxyalkyl” refers to an alkyl group having 1 or 6carbon atoms as defined above, wherein some or all of the hydrogen atomsin these groups may be replaced by OH groups.

The term “C₁-C₄-alkoxy-C₁-C₄-alkyl” refers to alkyl having 1 to 4 carbonatoms (as defined above), where According to one hydrogen atom of thealkyl radical is replaced by a C₁-C₄-alkoxy group (as defined above).Likewise, the term “C₁-C₆-alkoxy-C₁-C₄-alkyl” refers to alkyl having 1to 4 carbon atoms (as defined above), where According to one hydrogenatom of the alkyl radical is replaced by a C₁-C₆-alkoxy group (asdefined above).

The term “C₂-C₆-alkenyl” refers to a straight-chain or branchedunsaturated hydrocarbon radical having 2 to 6 carbon atoms and a doublebond in any position. Examples are “C₂-C₄-alkenyl” groups, such asethenyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl,2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl.

The term “C₂-C₆-alkynyl” refers to a straight-chain or branchedunsaturated hydrocarbon radical having 2 to 6 carbon atoms andcontaining at least one triple bond. Examples are “C₁-C₄-alkynyl”groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl),but-1-ynyl, but-2-ynyl, but-3-ynyl, 1-methyl-prop-2-ynyl.

The term “C₁-C₆-alkoxy” refers to a straight-chain or branched alkylgroup having 1 to 6 carbon atoms which is bonded via an oxygen, at anyposition in the alkyl group. Examples are “C₁-C₄-alkoxy” groups, such asmethoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methyl, propoxy,2-methylpropoxy or 1,1-dimethylethoxy.

The term “C₁-C₆-halogenalkoxy” refers to a C₁-C₆-alkoxy radical asdefined above, wherein some or all of the hydrogen atoms in these groupsmay be replaced by halogen atoms as mentioned above. Examples are“C₁-C₄-halogenalkoxy” groups, such as OCH₂F, OCHF₂, OCF₃, OCH₂Cl,OCHCl₂, OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy,2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC₂F₅,2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoro,propoxy, 2 chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy,2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy,3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅,1-fluoromethyl-2-fluoroethoxy, 1-chloromethyl-2-chloroethoxy,1-bromomethyl-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy or nonafluorobutoxy.

The term “C₂-C₆-alkenyloxy” refers to a straight-chain or branchedalkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen,at any position in the alkenyl group. Examples are “C₂-C₄-alkenyloxy”groups.

The term “C₂-C₆-alkynyloxy” refers to a straight-chain or branchedalkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen,at any position in the alkynyl group. Examples are “C₂-C₄-alkynyloxy”groups.

The term “C₃-C₆-cycloalkyl” refers to monocyclic saturated hydrocarbonradicals having 3 to 6 carbon ring members, such as cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-,four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl orcarbocycle is a “C₃-C₁₀-cycloalkyl”.

The term “C₃-C₆-cycloalkenyl” refers to a monocyclic partiallyunsaturated 3-, 4- 5- or 6-membered carbocycle having 3 to 6 carbon ringmembers and at least one double bond, such as cyclopentenyl,cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturatedthree-, four-, five-, six-, seven-, eight-, nine or ten-memberedcarbocyclyl or carbocycle is a “C₃-C₁₀-cycloalkenyl”.

The term “C₃-C₈-cycloalkyl-C₁-C₄-alkyl” refers to alkyl having 1 to 4carbon atoms (as defined above), where According to one hydrogen atom ofthe alkyl radical is replaced by a cycloalkyl radical having 3 to 8carbon atoms (as defined above).

The term “C₁-C₆-alkylthio” as used herein refers to straight-chain orbranched alkyl groups having 1 to 6 carbon atoms (as defined above)bonded via a sulfur atom. Accordingly, the term “C₁-C₆-halogenalkylthio”as used herein refers to straight-chain or branched halogenalkyl grouphaving 1 to 6 carbon atoms (as defined above) bonded through a sulfuratom, at any position in the halogenalkyl group.

The term “C(═O)—C₁-C₆-alkyl” refers to a radical which is attachedthrough the carbon atom of the group C(═O) as indicated by the numbervalence of the carbon atom. The number of valence of carbon is 4, thatof nitrogen is 3. Likewise the following terms are to be construed:NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C₃-C₆-cycloalkyl),N(C₃-C₆-cycloalkyl)₂, C(═O)—NH(C₁-C₆-alkyl), C(═O)—N(C₁-C₆-alkyl)₂.

The term “saturated or partially unsaturated three-, four-, five-, six-,seven-, eight-, nine or ten-membered heterocyclyl or heterocycle,wherein the heterocyclyl or heterocycle contains 1, 2, 3 or 4heteroatoms selected from N, O and S” is to be understood as meaningboth saturated and partially unsaturated heterocycles, wherein the ringmember atoms of the heterocycle include besides carbon atoms 1, 2, 3 or4 heteroatoms independently selected from the group of O, N and S. Forexample:

a 3- or 4-membered saturated heterocycle which contains 1 or 2heteroatoms from the group consisting of O, N and S as ring members suchas oxirane, aziridine, thiirane, oxetane, azetidine, thiethane,[1,2]dioxetane, [1,2]dithietane, [1,2]diazetidine; anda 5- or 6-membered saturated or partially unsaturated heterocycle whichcontains 1, 2 or 3 heteroatoms from the group consisting of O, N and Sas ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl,2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl,3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl,3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl,3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl,4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl,5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl,3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl,4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl,4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl,4-isoxazolin-5-yl, 2-iso-thiazolin-3-yl, 3-isothiazolin-3-yl,4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl,4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl,4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydro-pyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl,2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl,3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl,4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl,1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl and also thecorresponding -ylidene radicals; anda 7-membered saturated or partially unsaturated heterocycle such astetra- and hexahydroazepinyl, such as2,3,4,5-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6- or -7-yl,3,4,5,6-tetrahydro[2H]azepin-2-,-3-,-4-,-5-,-6- or -7-yl,2,3,4,7-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6- or -7-yl,2,3,6,7-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6- or -7-yl,hexahydroazepin-1-,-2-,-3- or -4-yl, tetra- and hexahydrooxepinyl suchas 2,3,4,5-tetrahydro[1H]oxepin-2-,-3-,-4-,-5-,-6- or -7-yl,2,3,4,7-tetrahydro[1H]oxepin-2-,-3-,-4-,-5-,-6- or -7-yl,2,3,6,7-tetrahydro[1H]oxepin-2-, -3-,-4-,-5-,-6- or -7-yl,hexahydroazepin-1-,-2-,-3- or -4-yl, tetra- andhexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra-and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl,tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyland the corresponding -ylidene radicals.

The term “substituted” refers to substituted with 1, 2, 3 or up to themaximum possible number of substituents.

The term “5- or 6-membered heteroaryl” or “5- or 6-memberedheteroaromatic” refers to aromatic ring systems including besides carbonatoms, 1, 2, 3 or 4 heteroatoms independently selected from the groupconsisting of N, O and S, for example,

a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl,thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl,pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl,imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl,isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl,thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl; ora 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl,pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and1,2,4-triazin-3-yl.

Agriculturally acceptable salts of the inventive compounds encompassespecially the salts of those cations or the acid addition salts ofthose acids whose cations and anions, respectively, have no adverseeffect on the fungicidal action of said compounds. Suitable cations arethus in particular the ions of the alkali metals, preferably sodium andpotassium, of the alkaline earth metals, preferably calcium, magnesiumand barium, of the transition metals, preferably manganese, copper, zincand iron, and also the ammonium ion which, if desired, may carry one tofour C₁-C₄-alkyl substituents and/or one phenyl or benzyl substituent,preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium,trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions,preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferablytri(C₁-C₄-alkyl)sulfoxonium. Anions of useful acid addition salts areprimarily chloride, bromide, fluoride, hydrogensulfate, sulfate,dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate,carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and theanions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionateand butyrate. They can be formed by reacting such inventive compoundwith an acid of the corresponding anion, preferably of hydrochloricacid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The inventive compounds can be present in atropisomers arising fromrestricted rotation about a single bond of asymmetric groups. They alsoform part of the subject matter of the present invention.

Depending on the substitution pattern, the compounds of formula I andtheir N-oxides may have one or more centers of chirality, in which casethey are present as pure enantiomers or pure diastereomers or asenantiomer or diastereomer mixtures. Both, the pure enantiomers ordiastereomers and their mixtures are subject matter of the presentinvention.

In the following, particular embodiments of the inventive compounds aredescribed. Therein, specific meanings of the respective substituents arefurther detailed, wherein the meanings are in each case on their own butalso in any combination with one another, particular embodiments of thepresent invention.

Furthermore, in respect of the variables, generally, the embodiments ofthe compounds I also apply to the intermediates.

R¹ is in each case independently selected from halogen, OH, NO₂, SH,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C₂-C₄-alkenyl), N(C₂-C₄-alkenyl)₂,NH(C₂-C₄-alkynyl), N(C₂-C₄-alkynyl)₂, NH(C₃-C₆-cycloalkyl),N(C₃-C₆-cycloalkyl)₂, N(C₂-C₄-alkyl)(C₂-C₄-alkenyl),N(C₂-C₄-alkyl)(C₂-C₄-alkynyl), N(C₂-C₄-alkyl)(C₃-C₆-cycloalkyl),N(C₂-C₄-alkenyl)(C₂-C₄-alkynyl), N(C₂-C₄-alkenyl)(C₃-C₆-cycloalkyl),N(C₂-C₄-alkynyl)(C₃-C₆-cycloalkyl), NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl), NH—SO₂—R^(x), S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)-aryl,C₁-C₆-cycloalkylthio, S(O)_(m)—C₂-C₆-alkenyl, S(O)_(m)—C₂-C₆-alkynyl,CH(═O), C(═O)C₁-C₆-alkyl, C(═O)C₂-C₆-alkenyl, C(═O)C₂-C₆-alkynyl,C(═O)C₃-C₆-cycloalkyl, C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂,C(═O)N(C₂-C₆-alkenyl), C(═O)N(C₂-C₆-alkynyl), C(═O)N(C₃-C₇-cycloalkyl),CH(═S), C(═S)C₁-C₆-alkyl, C(═S)C₂-C₆-alkenyl, C(═S)C₂-C₆-alkynyl,C(═S)C₃-C₆-cycloalkyl, (═S)O(C₂-C₆-alkenyl), C(═S)O(C₂-C₆-alkynyl),C(═S)O(C₃-C₇-cycloalkyl), C(═S)NH(C₁-C₆-alkyl), C(═S)NH(C₂-C₆-alkenyl),C(═S)NH(C₂-C₆-alkynyl), C(═S)NH(C₃-C₇-cycloalkyl), C(═S)N(C₁-C₆-alkyl)₂,C(═S)N(C₂-C₆-alkenyl), C(═S)N(C₂-C₆-alkynyl), C(═S)N(C₃-C₇-cycloalkyl),C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, OR^(Y), C₃-C₆-cycloalkyl,five- or six-membered heteroaryl and aryl; wherein the heteroarylcontains one, two or three heteroatoms selected from N, O and S; wherein

-   R^(x) is C₁-C₄-alkyl, C₁-C₄-halogenalkyl, unsubstituted aryl or aryl    that is substituted by 1, 2, 3, 4 or 5 substituents R^(x1)    independently selected from C₁-C₄-alkyl, halogen, OH, CN,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;-   R^(Y) is C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,    C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl; phenyl and    phenyl-C₁-C₆-alkyl; wherein the phenyl group is unsubstituted or    substituted with substituents selected from the group consisting of    halogen, CN, OH, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy and    C₁-C₆-halogenalkoxy;    wherein the acyclic moieties of R¹ are unsubstituted or substituted    with groups Ra which independently of one another are selected from:-   R^(1a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl    and phenoxy, wherein the aryl and phenoxy group is unsubstituted or    substituted with substituents R^(11a) selected from the group    consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    wherein the carbocycle, heteroaryl and aryl moieties of R¹ are    unsubstituted or substituted with groups R^(1a) which independently    of one another are selected from:-   R^(1b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.    and wherein m is 0, 1 and 2.

According to one embodiment of formula I, R¹ is selected from the groupconsisting of halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl, C₁-C₆-alkoxy,C₁-C₆-halogenalkoxy, C₃-C₆-cycloalkyl and C₃-C₆-halogencycloalkyl.

According to still another embodiment of formula I, R¹ is halogen, inparticular F, Cl, Br or I, more specifically F, Cl or Br, in particularF or Cl.

According to still another embodiment of formula I, R¹ is F.

According to still another embodiment of formula I, R¹ is Cl.

According to still another embodiment of formula I, R¹ is Br.

According to still another embodiment of formula I, R¹ is OH.

According to still another embodiment of formula I, R¹ is NO₂.

According to still another embodiment of formula I, R¹ is SH.

According to still another embodiment of formula I, R¹ is,NH(C₁-C₄-alkyl), in particular NH(CH₃), NH(C₂H₅).

According to still another embodiment of formula I, R is,N(C₁-C₄-alkyl)₂, in particular NH(CH₃)₂, NH(C₂H₅)₂.

According to still another embodiment of formula I, R¹ is,NH(C₂-C₄-alkenyl), in particular NH(CH═CH₂), NH(CH₂CH═CH₂).

According to still another embodiment of formula I, R¹ is,N(C₂-C₄_-alkenyl)₂, in particular N(CH═CH₂)₂, N(CH₂CH═CH₂)₂.

According to still another embodiment of formula I, R¹ is,NH(C₂-C₄-alkynyl), in particular NH(C≡CH), NH(CH₂C≡CH).

According to still another embodiment of formula I, R¹ is,N(C₂-C₄-alkynyl)₂, in particular N(C≡CH)₂, N(CH₂C≡CH)₂.

According to still another embodiment of formula I, R¹ is,NH(C₃-C₆-cycloalkyl), in particular NH(C₃H), NH(C₄H₉).

According to still another embodiment of formula I, R¹ is,N(C₃-C₆-cycloalkyl)₂, in particular N(C₃H₇)₂, N(C₄H₉)₂.

According to still another embodiment of formula I, R isN(C₁-C₄-alkyl)(C₂-C₄-alkenyl), in particular N(CH₃)(CH═CH₂),N(CH₃)(CH₂CH═CH₂), N(C₂H₅)(CH═CH₂), N(C₂H₅)(CH₂CH═CH₂).

According to still another embodiment of formula I, R isN(C₁-C₄-alkyl)(C₂-C₄-alkynyl), in particular N(CH₃)(C≡CH),N(CH₃)(CH₂C≡CH), N(C₂H₅)(C≡CH), N(C₂H₅)(CH₂C≡CH).

According to still another embodiment of formula I, R isN(C₁-C₄-alkyl)(C₃-C₆-cycloalkyl), in particular N(CH₃)(C₃H₇),N(CH₃)(C₄H₉), N(C₂H₅)(C₃H₇), N(CH₃)(C₄H₉).

According to still another embodiment of formula I, R isN(C₂-C₄-alkenyl)(C₂-C₄-alkynyl), in particular N(CH═CH₂)(C≡CH),N(CH₂CH═CH₂)(CH₂C≡CH), N(CH═CH₂)(C≡CH), N(CH₂CH═CH₂)(CH₂C≡CH).

According to still another embodiment of formula I, R isN(C₂-C₄-alkenyl)(C₃-C₆-cycloalkyl), in particular N(CH═CH₂)(C₃H₇),N(CH₂CH═CH₂)(C₄H₉), N(CH═CH₂)(C₃H₇), N(CH₂CH═CH₂)(C₄H₉).

According to still another embodiment of formula I, R isN(C₂-C₄-alkynyl)(C₃-C₆-cycloalkyl), in particular N(C≡CH)(C₃H),N(CH₂C≡CH)(C₄H₉), N(C≡CH)(C₃H), N(CH₂C≡CH)(C₄H₉).

According to still another embodiment of formula I, R¹ is,NH(C(═O)(C₁-C₄-alkyl), in particular NH(C(═O)(CH₃), NH(C(═O)(C₂H₅).

According to still another embodiment of formula I, R¹ isN(C(═O)(C₁-C₄-alkyl)₂, in particular N(C(═O)(CH₃)₂, N(C(═O)(C₂H₅)₂.

According to a further specific embodiment of formula I, R¹ isNH—SO₂—R^(x) such as NH—SO₂—CH₃, NH—SO₂—CH₂—CH₃, NH—SO₂—CF₃, NH—SO₂-Ts.

According to still another embodiment of formula I, R¹ isS(O)_(m)—C₁-C₆-alkyl such as SCH₃, S(═O) CH₃, S(O)₂CH₃.

According to still another embodiment of formula I, R¹ is S(O)_(m)-arylsuch as S-phenyl, S(═O) phenyl, S(O)₂phenyl.

According to still another embodiment of formula I, R¹ isS(O)_(m)—C₂-C₆-alkenyl such as SCH═CH₂, S(═O)CH═CH₂, S(O)₂CH═CH₂,SCH₂CH═CH₂, S(═O)CH₂CH═CH₂, S(O)₂CH₂CH═CH₂.

According to still another embodiment of formula I, R¹ isS(O)_(m)—C₂-C₆-alkynyl such as SC≡CH, S(═O)C≡CH, S(O)₂C≡CH, SCH₂C≡CH,S(═O)CH₂C≡CH, S(O)₂CH₂C≡CH.

According to a further specific embodiment of formula I, R¹ is CH(═O).

According to a further specific embodiment of formula I, R isC(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl) orC(═O)N(C₁-C₆-alkyl)₂, wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R isC(═O)C₂-C₆-alkenyl, C(═O)O(C₂-C₆-alkenyl), (═O)NH(C₂-C₆-alkenyl) orC(═O)N(C₂-C₆-alkenyl)₂, wherein alkenyl is CH═CH₂, CH₂CH═CH₂.

According to a further specific embodiment of formula I, R isC(═O)C₂-C₆-alkynyl, C(═O)O(C₂-C₆-alkynyl), C(═O)NH(C₂-C₆-alkynyl) orC(═O)N(C₂-C₆-alkynyl)₂, wherein alkynyl is C≡CH, CH₂C≡CH.

According to a further specific embodiment of formula I, R isC(═O)C₃-C₆-cycloalkyl, C(═O)O(C₃-C₆-cycloalkyl),C(═O)NH(C₃-C₆-cycloalkyl) or C(═O)N(C₃-C₇-cycloalkyl)₂, whereincycloalkyl is cyclopropyl (C₃H₇) or cyclobutyl (C₄H₉).

According to a further specific embodiment of formula I, R¹ is CH(═S).

According to a further specific embodiment of formula I, R isC(═S)C₁-C₆-alkyl, C(═S)OC₁-C₆-alkyl, C(═S)NH(C₁-C₆-alkyl) orC(═S)NH(C₁-C₆-alkyl), wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R isC(═S)C₂-C₆-alkenyl, C(═S)OC₂-C₆-alkenyl, C(═S)NH(C₂-C₆-alkenyl) orC(═S)N(C₂-C₆-alkenyl)₂, wherein alkenyl is CH═CH₂, CH₂CH═CH₂.

According to a further specific embodiment of formula I, R isC(═S)C₂-C₆-alkynyl, C(═S)O(C₂-C₆-alkynyl), C(═S)NH(C₂-C₆-alkynyl) orC(═S)N(C₂-C₆-alkynyl)₂, wherein alkynyl is C≡CH, CH₂C≡CH.

According to a further specific embodiment of formula I, R¹ isC(═S)C₃-C₆-cycloalkyl, C(═S)O(C₃-C₇-cycloalkyl),C(═S)NH(C₃-C₇-cycloalkyl) or, C(═S)N(C₃-C₇-cycloalkyl)₂, whereincycloalkyl is cyclopropyl (C₃H₇) or cyclobutyl (C₄H₉).

According to still another embodiment of formula I, R¹ is C₁-C₆-alkyl,in particular C₁-C₄-alkyl, such as CH₃. or C₂₅, in particular CH₃ orCH₂CH₃.

According to still another embodiment of formula I, R¹ isC₁-C₆-halogenalkyl, in particular C₁-C₄-halogenalkyl, such as CF₃, CCl₃,FCH₂, ClCH₂, F₂CH, C₂CH, CF₃CH₂, CCl₃CH₂ or CF₂CHF₂.

According to still a further embodiment of formula I, R¹ isC₂-C₆-alkenyl, in particular C₂-C₄-alkenyl, such as CH═CH₂, C(CH₃)═CH₂,CH₂CH═CH₂.

According to a further specific embodiment of formula I, R¹ isC₂-C₆-halogenalkenyl, in particular C₂-C₄-halogenalkenyl, morespecifically C₂-C₃-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF₂,CH═CCl₂, CH₂CH═CHF, CH₂CH═CHCl, CH₂CH═CF₂, CH₂CH═CCl₂, CF₂CH═CF₂,CCl₂CH═CCl₂, CF₂CF═CF₂, CCl₂CCl═CCl₂.

According to still a further embodiment of formula I, R is C₂-C₆-alkynylor C₂-C₆-halogenalkynyl, in particular C₂-C₄-alkynyl orC₂-C₄-halogenalkynyl, such as C≡CH, CH₂C≡CH, C≡CCl, CH₂C≡CCl, orCCl₂C≡CCl.

According to a further specific embodiment of formula I, R¹ is ORwherein R is C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl.

According to a further specific embodiment of formula I, R¹ is OR^(Y)wherein R^(Y) is C₁-C₆-alkyl, in particular C₁-C₄-alkyl, morespecifically C₁-C₂-alkoxy. R¹ is such as OCH₃ or OCH₂CH₃.

According to a further specific embodiment of formula I, R¹ is ORwherein R is C₁-C₆-halogenalkyl, in particular C₁-C₄-halogenalkyl, morespecifically C₁-C₂-halogenalkyl. R¹ is such as OCF₃, OCHF₂, OCH₂F,OCCl₃, OCHCl₂ or OCH₂Cl, in particular OCF₃, OCHF₂, OCCl₃ or OCHCl₂.

According to a further specific embodiment of formula I, R¹ is ORwherein R C₂-C₆-alkenyl, in particular C₂-C₄-alkenyl, more specificallyC₁-C₂-alkenyl. R¹ is such as OCH═CH₂, OCH₂CH═CH₂.

According to a further specific embodiment of formula I, R¹ is OR^(Y),wherein R C₂-C₆-halogenalkenyl, in particular C₂-C₄-halogenalkenyl, morespecifically C₁-C₂-halogenalkenyl.

According to a further specific embodiment of formula I, R¹ is ORwherein R C₂-C₆-alkynyl, in particular C₂-C₆-alkynyl, in particularC₂-C₄-alkynyl, more specifically C₁-C₂-alkynyl. R¹ is such as OC≡CH,

According to a further specific embodiment of formula I, R¹ is OR^(Y),wherein R C₂-C₆-halogenalkynyl, in particular C₂-C₆-halogenalkynyl, inparticular C₂-C₄-halogenalkynyl, more specifically C₁-C₂-halogenalkynyl.R¹ is such as OC≡CCl, OCH₂C≡CCl, or OCCl₂C≡CCl.

According to still another embodiment of formula I, R¹ is OR wherein RC₃-C₆-cycloalkenyl, in particular cyclopropenyl.

According to still another embodiment of formula I, R¹ isC₃-C₆-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I, R¹ isC₃-C₆-halogencycloalkyl. In a special embodiment R^(1b) is fully orpartially halogenated cyclopropyl, such as 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl.

According to still another embodiment of formula I, R¹ isphenyl-C₁-C₆-alkyl, such as phenyl-CH₂, wherein the phenyl moiety ineach case is unsubstituted or substituted by one, two or three identicalor different groups R^(1b) which independently of one another areselected from halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl andC₁-C₂-halogenalkoxy, in particular F, Cl, Br, CH₃, OCH₃, CF₃ and OCF₃.

According to still another embodiment of formula I, R¹ is aryl, inparticular phenyl, wherein the aryl or phenyl moiety in each case isunsubstituted or substituted with identical or different groups R^(1b)which independently of one another are selected from CN, halogen,C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl and C₁-C₂-halogenalkoxy,in particular CN, F, C, Br, CH₃, OCH₃, CHF₂, OCHF₂, CF₃ and OCF₃.According to one embodiment, R¹ is unsubstituted phenyl. According toanother embodiment, R¹ is phenyl, that is substituted with one, two orthree, in particular one, halogen, in particular selected from F, Cl andBr, more specifically selected from F and Cl.

According to still another embodiment of formula I, R¹ is a 5-memberedheteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl,thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl,pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl,imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl,isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl,1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.

According to still another embodiment of formula I, R¹ is a 6-memberedheteroaryl such as pyri-din-2-yl, pyridin-3-yl, pyridin-4-yl,pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and1,2,4-triazin-3-yl.

According to still another embodiment of formula I, R¹ is in each caseindependently selected from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl, C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl,C₂-C₆-halogenalkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl andC₃-C₆-halogencycloalkyl, wherein the acyclic moieties of R¹ areunsubstituted or substituted with identical or different groups R^(1a)as defined and preferably defined herein, and wherein the carbocyclic,phenyl and heteroaryl moieties of R¹ are unsubstituted or substitutedwith identical or different groups R^(1b) as defined and preferablydefined herein.

According to still another embodiment of formula I, R¹ is in each caseindependently selected from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy; whereinthe acyclic moieties of R¹ are unsubstituted or substituted withidentical or different groups R^(1a) as defined and preferably definedherein.

According to still another embodiment of formula I, R¹ is in each caseindependently selected from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkynyl, OR^(Y), C₃-C₆-cycloalkyl; wherein R is C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl.

R^(1a) are the possible substituents for the acyclic moieties of R¹.

According to one embodiment R^(1a) is independently selected fromhalogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl andphenoxy, wherein the aryl and phenyl group is unsubstituted orsubstituted with substituents R^(11a) selected from the group consistingof halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy.

According to one embodiment R^(1a) is independently selected fromhalogen, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl andC₁-C₄-halogenalkoxy. Specifically, R^(1a) is independently selected fromF, Cl, Br, I, C₁-C₂-alkoxy, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl andC₁-C₂-halogenalkoxy.

According to still another embodiment of formula I, R^(1a) isindependently halogen, in particular selected from F, Cl, Br and I, morespecifically F, Cl and Br.

R^(1b) are the possible substituents for the carbocyclic, heteroaryl andphenyl moieties of R¹. R^(1b) according to the invention isindependently selected from halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy and C₁-C₆-akylthio.

According to one embodiment thereof R^(1b) is independently selectedfrom halogen, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl andC₁-C₄-halogenalkoxy, in particular halogen, C₁-C₄-alkyl andC₁-C₄-alkoxy. Specifically, R is independently selected from F, Cl, CN,CH₃, OCH₃ and halogenmethoxy.

Particularly preferred embodiments of R¹ according to the invention arein Table P1 below, wherein each line of lines P1-1 to P1-40 correspondsto one particular embodiment of the invention, wherein P1-1 to P1-40 arealso in any combination with one another a preferred embodiment of thepresent invention. The connection point to the carbon atom, to which R¹is bound is marked with “#” in the drawings.

TABLE P1 No. R¹ P1-1 CH₃ P1-2 CH₂F P1-3 CHF₂ P1-4 CF₃ P1-5 C₂H₅ P1-6CH(CH₃)₂ P1-7 CH₂CH₂CH₃ P1-8 CH₂CH₂CH₂CH₃ P1-9 CH₂CH(CH₃)₂ P1-10 C(CH₃)₃P1-11 CH₂CH₂CH₂CH₂CH₃ P1-12 CH═CH₂ P1-13 CH₂CH═CH₂ P1-14 C≡CH P1-15CH₂C≡CH P1-16 CH₂CH₂CH(CH₃)₂ P1-17 OH P1-18 OCH₃ P1-19 OCHF₂ P1-20 OC₂H₅P1-21 F P1-22 Cl P1-23 Br P1-24 NO₂ P1-25 CO—NH₂ P1-26 CO—NH(CH₃) P1-27CO—N(CH₃)₂ P1-28 HNCH₃ P1-29 HNC₂H₅ P1-30 (CH₃)₂N P1-31 SO₂H P1-32SO₂—CH₃ P1-33 SO—CH₃ P1-34 S—CH₃ P1-35

P1-36

P1-37

P1-38

P1-39

P1-40

R² is in each case independently selected from halogen, OH, NO₂, SH,NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C₂-C₄-alkenyl),N(C₂-C₄-alkenyl)₂, NH(C₂-C₄-alkynyl), N(C₂-C₄-alkynyl)₂,NH(C₃-C₆-cycloalkyl), N(C₃-C₆-cycloalkyl)₂,N(C₂-C₄-alkyl)(C₂-C₄-alkenyl), N(C₂-C₄-alkyl)(C₂-C₄-alkynyl),N(C₂-C₄-alkyl)(C₃-C₆-cycloalkyl), N(C₂-C₄-alkenyl)(C₂-C₄-alkynyl),N(C₂-C₄-alkenyl)(C₃-C₆-cycloalkyl), N(C₂-C₄-alkynyl)(C₃-C₆-cycloalkyl),NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x),S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)-aryl, C₁-C₆-cycloalkylthio,S(O)_(m)—C₂-C₆-alkenyl, S(O)_(m)—C₂-C₆-alkynyl, CH(═O),C(═O)C₁-C₆-alkyl, C(═O)C₂-C₆-alkenyl, C(═O)C₂-C₆-alkynyl,C(═O)C₃-C₆-cyclpalkyl, C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂,C(═O)N(C₂-C₆-alkenyl)₂, C(═O)N(C₂-C₆-alkynyl)₂,C(═O)N(C₃-C₇-cycloalkyl)₂, CH(═S), C(═S)C₁-C₆-alkyl, C(═S)C₂-C₆-alkenyl,C(═S)C₂-C₆-alkynyl, C(═S)C₃-C₆-cyclpalkyl, C(═S)O(C₂-C₆-alkenyl),C(═S)O(C₂-C₆-alkynyl), C(═S)O(C₃-C₇-cycloalkyl), C(═S)NH(C₁-C₆-alkyl),C(═S)NH(C₂-C₆-alkenyl), C(═S)NH(C₂-C₆-alkynyl),C(═S)NH(C₃-C₇-cycloalkyl), C(═S)N(C₁-C₆-alkyl)₂, C(═S)N(C₂-C₆-alkenyl)₂,C(═S)N(C₂-C₆-alkynyl)₂, C(═S)N(C₃-C₇-cycloalkyl)₂, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, OR^(Y), C₃-C₆-cycloalkyl, five- orsix-membered heteroaryl and aryl; wherein the heteroaryl contains one,two or three heteroatoms selected from N, O and S; wherein

-   R^(x) is as defined above;-   R^(Y) is as defined above;    wherein the acyclic moieties of R² are unsubstituted or substituted    with groups R^(2a) which independently of one another are selected    from:-   R^(2a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl    and phenoxy, wherein the aryl and phenyl group is unsubstituted or    substituted with substituents R^(21a) selected from the group    consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    wherein the carbocyclic, heteroaryl and aryl moieties of R² are    unsubstituted or substituted with groups R^(2b) which independently    of one another are selected from:-   R^(2b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

According to one embodiment of formula I, R² is selected from the groupconsisting of halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl, C₁-C₆-alkoxy,C₁-C₆-halogenalkoxy and OR^(Y).

R² is selected from the group consisting of halogen, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl,C₂-C₆-halogenalkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy andC₃-C₆-halogencycloalkyl.

According to still another embodiment of formula I, R² is halogen, inparticular F, Cl, Br or I, more specifically F, Cl or Br, in particularF or Cl.

According to still another embodiment of formula I, R² is F.

According to still another embodiment of formula I, R² is Cl.

According to still another embodiment of formula I, R² is Br.

According to still another embodiment of formula I, R² is OH.

According to still another embodiment of formula I, R² is NO₂.

According to still another embodiment of formula I, R² is SH.

According to still another embodiment of formula I, R² is NH₂.

According to still another embodiment of formula I, R² is,NH(C₁-C₄-alkyl), in particular NH(CH₃), NH(C₂H₅).

According to still another embodiment of formula I, R² isN(C₁-C₄-alkyl)₂, in particular NH(CH₃)₂, NH(C₂H₅)₂.

According to still another embodiment of formula I, R² isNH(C₂-C₄-alkenyl), in particular NH(CH═CH₂), NH(CH₂CH═CH₂).

According to still another embodiment of formula I, R² isN(C₂-C₄_-alkenyl)₂, in particular N(CH═CH₂)₂, N(CH₂CH═CH₂)₂.

According to still another embodiment of formula I, R² is,NH(C₂-C₄-alkynyl), in particular NH(C≡CH), NH(CH₂C≡CH).

According to still another embodiment of formula I, R² is,N(C₂-C₄-alkynyl)₂, in particular N(C≡CH)₂, N(CH₂C≡CH)₂.

According to still another embodiment of formula I, R² is,NH(C₃-C₆-cycloalkyl), in particular NH(C₃H), NH(C₄H₉).

According to still another embodiment of formula I, R² is,N(C₃-C₆-cycloalkyl)₂, in particular N(C₃H₇)₂, N(C₄H₉)₂.

According to still another embodiment of formula I, R² isN(C₁-C₄-alkyl)(C₂-C₄-alkenyl), in particular N(CH₃)(CH═CH₂),N(CH₃)(CH₂CH═CH₂), N(C₂H₅)(CH═CH₂), N(C₂H₅)(CH₂CH═CH₂).

According to still another embodiment of formula I, R² isN(C₁-C₄-alkyl)(C₂-C₄-alkynyl), in particular N(CH₃)(C≡CH),N(CH₃)(CH₂C≡CH), N(C₂H₅)(C≡CH), N(C₂H₅)(CH₂C≡CH).

According to still another embodiment of formula I, R² isN(C₁-C₄-alkyl)(C₃-C₆-cycloalkyl), in particular N(CH₃)(C₃H₇),N(CH₃)(C₄H₉), N(C₂H₅)(C₃H₇), N(CH₃)(C₄H₉).

According to still another embodiment of formula I, R² isN(C₂-C₄-alkenyl)(C₂-C₄-alkynyl), in particular N(CH═CH₂)(C≡CH),N(CH₂CH═CH₂)(CH₂C≡CH), N(CH═CH₂)(C≡CH), N(CH₂CH═CH₂)(CH₂C≡CH).

According to still another embodiment of formula I, R² isN(C₂-C₄-alkenyl)(C₃-C₆-cycloalkyl), in particular N(CH═CH₂)(C₃H₇),N(CH₂CH═CH₂)(C₄H₉), N(CH═CH₂)(C₃H₇), N(CH₂CH═CH₂)(C₄H₉).

According to still another embodiment of formula I, R² isN(C₂-C₄-alkynyl)(C₃-C₆-cycloalkyl), in particular N(C≡CH)(C₃H),N(CH₂C≡CH)(C₄H₉), N(C≡CH)(C₃H₇), N(CH₂C≡CH)(C₄H₉).

According to still another embodiment of formula I, R² is,NH(C(═O)(C₁-C₄-alkyl), in particular NH(C(═O)(CH₃), NH(C(═O)(C₂H₅).

According to still another embodiment of formula I, R² isN(C(═O)(C₁-C₄-alkyl)₂, in particular N(C(═O)(CH₃)₂, N(C(═O)(C₂H₅)₂.

According to a further specific embodiment of formula I, R² isNH—SO₂—R^(x) such as NH—SO₂—CH₃, NH—SO₂—CH₂—CH₃, NH—SO₂—CF₃, NH—SO₂-Ts.

According to still another embodiment of formula I, R² isS(O)_(m)—C₁-C₆-alkyl such as SCH₃, S(═O) CH₃, S(O)₂CH₃.

According to still another embodiment of formula I, R² is S(O)_(m)-arylsuch as S-phenyl, S(═O) phenyl, S(O)₂phenyl.

According to still another embodiment of formula I, R² isS(O)_(m)—C₂-C₆-alkenyl such as SCH═CH₂, S(═O)CH═CH₂, S(O)₂CH═CH₂,SCH₂CH═CH₂, S(═O)CH₂CH═CH₂, S(O)₂CH₂CH═CH₂.

According to still another embodiment of formula I, R² isS(O)_(m)—C₂-C₆-alkynyl such as SC≡CH, S(═O)C≡CH, S(O)₂C≡CH, SCH₂C≡CH,S(═O)CH₂C≡CH, S(O)₂CH₂C≡CH.

According to a further specific embodiment of formula I, R² is CH(═O).

According to a further specific embodiment of formula I, R² isC(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl) orC(═O)N(C₁-C₆-alkyl)₂, wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R² isC(═O)C₂-C₆-alkenyl, C(═O)O(C₂-C₆-alkenyl), C(═O)NH(C₂-C₆-alkenyl) orC(═O)N(C₂-C₆-alkenyl)₂, wherein alkenyl is CH═CH₂, C(CH₃)═CH₂,CH₂CH═CH₂.

According to a further specific embodiment of formula I, R² isC(═O)C₂-C₆-alkynyl, C(═O)O(C₂-C₆-alkynyl), C(═O)NH(C₂-C₆-alkynyl) orC(═O)N(C₂-C₆-alkynyl)₂), wherein alkynyl is C≡CH, CH₂C≡CH,

According to a further specific embodiment of formula I, R² isC(═O)C₃-C₆-cycloalkyl, C(═O)O(C₃-C₆-cycloalkyl),C(═O)NH(C₃-C₆-cycloalkyl) or C(═O)N(C₃-C₇-cycloalkyl)₂, whereincycloalkyl is cyclopropyl (C₃H₇) or cyclobutyl (C₄H₉).

According to a further specific embodiment of formula I, R² is CH(═S).

According to a further specific embodiment of formula I, R² isC(═S)C₁-C₆-alkyl, C(═S)OC₁-C₆-alkyl, C(═S)NH(C₁-C₆-alkyl) orC(═S)NH(C₁-C₆-alkyl), wherein alkyl is CH₃, C₂H, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R² isC(═S)C₂-C₆-alkenyl, C(═S)OC₂-C₆-alkenyl, C(═S)NH(C₂-C₆-alkenyl) orC(═S)N(C₂-C₆-alkenyl)₂, wherein alkenyl is CH═CH₂, CH₂CH═CH₂.

According to a further specific embodiment of formula I, R² isC(═S)C₂-C₆-alkynyl, C(═S)O(C₂-C₆-alkynyl), C(═S)NH(C₂-C₆-alkynyl) orC(═S)N(C₂-C₆-alkynyl), wherein alkynyl is C≡CH, CH₂C≡CH.

According to a further specific embodiment of formula I, R² isC(═S)C₃-C₆-cycloalkyl, C(═S)O(C₃-C₇-cycloalkyl),C(═S)NH(C₃-C₇-cycloalkyl) or C(═S)N(C₃-C₇-cycloalkyl), whereincycloalkyl is cyclopropyl (C₃H₇) or cyclobutyl (C₄H₉).

According to still another embodiment of formula I, R² is C₁-C₆-alkyl,in particular C₁-C₄-alkyl, such as CH₃. or C₂H₅, in particular CH₃ orCH₂CH₃.

According to still another embodiment of formula I, R² isC₁-C₆-halogenalkyl, in particular C₁-C₄-halogenalkyl, such as CF₃, CCl₃,FCH₂, ClCH₂, F₂CH, C₂CH, CF₃CH₂, CCl₃CH₂ or CF₂CHF₂.

According to still a further embodiment of formula I, R² isC₂-C₆-alkenyl, in particular C₂-C₄-alkenyl, such as CH═CH₂.

According to a further specific embodiment of formula I, R² isC₂-C₆-halogenalkenyl, in particular C₂-C₄-halogenalkenyl, morespecifically C₂-C₃-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF₂,CH═CCl₂, CH₂CH═CHF, CH₂CH═CHCl, CH₂CH═CF₂, CH₂CH═CCl₂, CF₂CH═CF₂,CCl₂CH═CCl₂, CF₂CF═CF₂, CCl₂CCl═CCl₂.

According to still a further embodiment of formula I, R² isC₂-C₆-alkynyl or C₂-C₆-halogenalkynyl, in particular C₂-C₄-alkynyl orC₂-C₄-halogenalkynyl, such as C≡CH, CH₂, C≡CH, C≡CCl, CH₂C≡CCl, orCCl₂C≡CCl.

According to a further specific embodiment of formula I, R² is ORwherein R is C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl.

According to a further specific embodiment of formula I, R² is ORwherein R is C₁-C₆-alkyl, in particular C₁-C₄-alkyl, more specificallyC₁-C₂-alkoxy. R² is such as OCH₃ or OCH₂CH₃.

According to a further specific embodiment of formula I, R² is ORwherein R is C₁-C₆-halogenalkyl, in particular C₁-C₄-halogenalkyl, morespecifically C₁-C₂-halogenalkyl. R² is such as OCF₃, OCHF₂, OCH₂F,OCCl₃, OCHCl₂ or OCH₂Cl, in particular OCF₃, OCHF₂, OCCl₃ or OCHCl₂.

According to a further specific embodiment of formula I, R² is ORwherein R C₂-C₆-alkenyl, in particular C₂-C₄-alkenyl, more specificallyC₁-C₂-alkenyl. R² is such as OCH═CH₂, OCH₂CH═CH₂.

According to a further specific embodiment of formula I, R² is ORwherein R C₂-C₆-alkynyl, in particular C₂-C₆-alkynyl, in particularC₂-C₄-alkynyl, more specifically C₁-C₂-alkynyl. R² is such as OC≡CH,OC≡CCl, OCH₂C≡CCl, or OCCl₂C≡CCl

According to still another embodiment of formula R² is OR wherein R isC₃-C₆-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I, R² is OR^(Y) whereinR^(Y) is C₃-C₆-halogencycloalkyl. In a special embodiment R¹ is fully orpartially halogenated cyclopropyl.

According to still another embodiment of formula I, R² is OR wherein RC₃-C₆-cycloalkenyl, in particular cyclopropenyl.

According to still another embodiment of formula I, R² isC₃-C₆-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I, R² isC₃-C₆-halogencycloalkyl. In a special embodiment R^(2b) is fully orpartially halogenated cyclopropyl, such as 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl

According to still another embodiment of formula I, R² isphenyl-C₁-C₆-alkyl, such as phenyl-CH₂, wherein the phenyl moiety ineach case is unsubstituted or substituted by one, two or three identicalor different groups R^(2b) which independently of one another areselected from halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl andC₁-C₂-halogenalkoxy, in particular F, Cl, Br, CH₃, OCH₃, CF₃ and OCF₃.

According to still another embodiment of formula I, R² is aryl, inparticular phenyl, wherein the aryl or phenyl moiety in each case isunsubstituted or substituted with identical or different groups R^(2b)which independently of one another are selected from CN, halogen,C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl and C₁-C₂-halogenalkoxy,in particular CN, F, C, Br, CH₃, OCH₃, CHF₂, OCHF₂, CF₃ and OCF₃.According to one embodiment, R² is unsubstituted phenyl. According toanother embodiment, R² is phenyl, that is substituted with one, two orthree, in particular one, halogen, in particular selected from F, Cl andBr, more specifically selected from F and Cl.

According to still another embodiment of formula I, R² is a 5-memberedheteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl,thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl,pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl,imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl,isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl,1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.

According to still another embodiment of formula I, R⁹ is a 6-memberedheteroaryl such as pyri-din-2-yl, pyridin-3-yl, pyridin-4-yl,pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and1,2,4-triazin-3-yl.

According to still another embodiment of formula I, R² is in each caseindependently selected from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl, C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl,C₂-C₆-halogenalkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl andC₃-C₆-halogencycloalkyl, wherein the acyclic moieties of R² areunsubstituted or substituted with identical or different groups R^(2a)as defined and preferably defined herein, and wherein the carbocyclic,phenyl and heteroaryl moieties of R² are unsubstituted or substitutedwith identical or different groups R^(2b) as defined and preferablydefined herein.

According to still another embodiment of formula I, R² is in each caseindependently selected from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy; whereinthe acyclic moieties of R² are unsubstituted or substituted withidentical or different groups R^(2a) as defined and preferably definedherein.

According to still another embodiment of formula I, R² is in each caseindependently selected from CN, halogen, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkynyl, OR^(Y), C₃-C₆-cycloalkyl; whereinR^(Y) is C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl orC₂-C₆-alkynyl.

R^(2a) are the possible substituents for the acyclic moieties of R².

According to one embodiment R^(2a) is independently selected fromhalogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl andphenoxy, wherein the aryl and phenyl group is unsubstituted orsubstituted with substituents R^(21a) selected from the group consistingof halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy.

According to one embodiment R^(2a) is independently selected fromhalogen, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl andC₁-C₄-halogenalkoxy. Specifically, R^(2a) is independently selected fromF, C, Br, I, C₁-C₂-alkoxy, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl andC₁-C₂-halogenalkoxy.

According to still another embodiment of formula I, R^(2a) isindependently halogen, in particular selected from F, Cl, Br and I, morespecifically F, Cl and Br.

R² are the possible substituents for the carbocyclic, heteroaryl andphenyl moieties of R². R^(2b) according to the invention isindependently selected from halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

According to one embodiment thereof R^(2b) is independently selectedfrom halogen, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl andC₁-C₄-halogenalkoxy, in particular halogen, C₁-C₄-alkyl andC₁-C₄-alkoxy. Specifically, R^(2b) is independently selected from F, Cl,CN, CH₃, OCH₃ and halogenmethoxy.

Particularly preferred embodiments of R² according to the invention arein Table P2 below, wherein each line of lines P2-1 to P2-41 correspondsto one particular embodiment of the invention, wherein P2-1 to P2-41 arealso in any combination with one another a preferred embodiment of thepresent invention. The connection point to the carbon atom, to which R²is bound is marked with “#” in the drawings.

TABLE P2 No. R¹ P2-1 CH₃ P2-2 CH₂F P2-3 CHF₂ P2-4 CF₃ P2-5 C₂H₅ P2-6CH(CH₃)₂ P2-7 CH₂CH₂CH₃ P2-8 CH₂CH₂CH₂CH₃ P2-9 CH₂CH(CH₃)₂ P2-10 C(CH₃)₃P2-11 CH₂CH₂CH₂CH₂CH₃ P2-12 CH═CH₂ P2-13 CH₂CH═CH₂ P2-14 C≡CH P2-15CH₂C≡CH P2-16 CH₂CH₂CH(CH₃)₂ P2-17 OH P2-18 OCH₃ P2-19 OCHF₂ P2-20 OC₂H₅P2-21 F P2-22 Cl P2-23 Br P2-24 NO₂ P2-25 NH₂ P2-26 CO—NH₂ P2-27CO—NH(CH₃) P2-28 CO—N(CH₃)₂ P2-29 HNCH₃ P2-30 HNC₂H₅ P2-31 (CH₃)₂N P2-32SO₂H P2-33 SO₂—CH₃ P2-34 SO—CH₃ P2-35 S—CH₃ P2-36

P2-37

P2-38

P2-39

P2-40

P2-41

U according to the invention is N or CR³

According to one embodiment of formula I, U is N.

According to another embodiment of formula I, U is CR³

R³ according to the invention is in each case independently selectedfrom hydrogen, halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, five- or six-memberedheteroaryl and aryl; wherein the heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein R^(x) is C₁-C₄-alkyl,C₁-C₄-halogenalkyl, unsubstituted aryl or aryl that is substituted withone, two, three, four or five substituents R^(x3) independently selectedfrom C₁-C₄-alkyl, halogen, OH, CN, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy;wherein the acyclic moieties of R³ are unsubstituted or substituted withidentical or different groups R^(3a) which independently of one anotherare selected from:

-   R^(3a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalky, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl    and phenoxy, wherein the aryl and phenoxy group is unsubstituted or    substituted with R^(31a) selected from the group consisting of    halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and    C₁-C₄-halogenalkoxy;    wherein the carbocyclic, heteroaryl and aryl moieties of R³ are    unsubstituted or substituted with identical or different groups    R^(3b) which independently of one another are selected from:-   R^(3b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalky,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

For every R³ that is present in the inventive compounds, the followingembodiments and preferences apply independently of the meaning of theother R³ that may be present in the ring.

According to one embodiment of formula I, R³ is H, halogen orC₁-C₆-alkyl, in particular H, CH₃, Et, F, C, more specifically H, CH₃, For Cl most preferred H, F or Cl.

According to another of formula I, R³ is halogen, in particular Br, F orC, more specifically F or Cl.

According to another embodiment of formula I, R³ is F

According to another embodiment of formula I, R³ is Cl

According to another embodiment of formula I, R³ is Br.

According to still another embodiment of formula I, R³ is hydrogen.

According to still another embodiment of formula I, R³ is OH.

According to still another embodiment of formula I, R³ is CN.

According to still another embodiment of formula I, R³ is NO₂.

According to still another embodiment of formula I, R³ is SH.

In a further specific embodiment R³ is NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂ or NH—SO₂—R^(x), wherein R^(x) is C₁-C₄-alkyl,C₁-C₄-halogenalkyl, unsubstituted phenoxy or aryl that is substitutedwith one, two, three, four or five substituents R^(x3) independentlyselected from C₁-C₄-alkyl, halogen, OH, CN, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, or C₁-C₄-halogenalkoxy. In particular C₁-C₄-alkyl, such asNHCH₃ and N(CH₃)₂. In particular R^(x) is C₁-C₄-alkyl, and phenyl thatis substituted with one CH₃, more specifically SO₂—R^(x) is CH₃ andtosyl group (“Ts”).

According to still another embodiment of formula I, R³ is C₁-C₆-alkyl,in particular C₁-C₄-alkyl, such as CH₃ or CH₂CH₃.

According to still another embodiment of formula I, R³ isC₁-C₆-halogenalkyl, in particular C₁-C₄-halogenalkyl, such as CF₃, CHF₂,CH₂F, CCl₃, CHCl₂, CH₂Cl, CF₃CH₂, CCl₃CH₂ or CF₂CHF₂.

According to still a further embodiment, R³ is C₂-C₆-alkenyl orC₂-C₆-halogenalkenyl, in particular C₂-C₄-alkenyl orC₂-C₄-halogenalkenyl, such as CH═CH₂, CH═CCl₂, CH═CF₂, CCl═CCl₂, CF═CF₂,CH═CH₂, CH₂CH═CCl₂, CH₂CH═CF₂, CH₂CCl═CCl₂, CH₂CF═CF₂, CCl₂CH═CCl₂,CF₂CH═CF₂, CCl₂CCl═CCl₂, or CF₂CF═CF₂.

According to still a further embodiment, R³ is C₂-C₆-alkynyl orC₂-C₆-halogenalkynyl, in particular C₂-C₄-alkynyl orC₂-C₄-halogenalkynyl, such as C≡CH, C≡CCl, C≡CF. CH₂C≡CH, CH₂C≡CCl, orCH₂C≡CF.

According to still another embodiment of formula I, R³ is C₁-C₆-alkoxy,in particular C₁-C₄-alkoxy, more specifically C₁-C₂-alkoxy such as OCH₃or OCH₂CH₃.

According to still another embodiment of formula I, R³ isC₁-C₆-halogenalkoxy, in particular C₁-C₄-halogenalkoxy, morespecifically C₁-C₂-halogenalkoxy such as OCF₃, OCHF₂, OCH₂F, OCCl₃,OCHCl₂ or OCH₂Cl, in particular OCF₃, OCHF₂, OCCl₃ or OCHCl₂.

In a further specific embodiment R³ is C₃-C₆-cycloalkyl, in particularcyclopropyl.

In a further specific embodiment, R³ is C₃-C₆-cycloalkyl, for examplecyclopropyl, substituted with one, two, three or up to the maximumpossible number of identical or different groups R^(3b) as defined andpreferably herein.

According to still another embodiment of formula I, R³ isC₃-C₆-halogencycloalkyl. In a special embodiment R³ is fully orpartially halogenated cyclopropyl.

According to still another embodiment of formula I, R³ is unsubstitutedaryl or aryl that is substituted with one, two, three or four R^(3b), asdefined herein. In particular, R³ is unsubstituted phenyl or phenyl thatis substituted with one, two, three or four R^(3b), as defined herein.

According to still another embodiment of formula I, R³ is unsubstituted5- or 6-membered heteroaryl. According to still a further embodiment, R³is 5- or 6-membered heteroaryl that is substituted with one, two orthree R^(3b), as defined herein.

According to still another embodiment of formula I, R³ is in each caseindependently selected from hydrogen, halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy and C₃-C₆-cycloalkyl; whereinthe acyclic moieties of R³ are not further substituted or carry one,two, three, four or five identical or different groups R^(3a) as definedbelow and wherein the cycloalkyl moieties of R³ are not furthersubstituted or carry one, two, three, four or five identical ordifferent groups R^(3b) as defined below.

According to still another embodiment of formula I, R³ is independentlyselected from hydrogen, halogen, CN, OH, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, wherein the acyclic andcyclic moieties of R³ are unsubstituted or substituted by halogen.

According to still another embodiment of formula I, R³ is independentlyselected from hydrogen, halogen, OH, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₁-C₆-alkoxy and C₁-C₆-halogenalkoxy, in particular independentlyselected from H, F, C, Br, CN, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy.

According to still another embodiment of formula I, R³ is independentlyselected from H, CN, halogen or C₁-C₆-alkyl, in particular H, CN, CH₃,Et, F, Cl, more specifically H, CN, CH₃, F or C most preferred H, CH₃, For Cl.

R^(3a) are the possible substituents for the acyclic moieties of R³.

R^(3a) according to the invention is independently selected fromhalogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalky,C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl and phenoxy, wherein the aryland phenoxy group is unsubstituted or substituted with R^(33a) selectedfrom the group consisting of halogen, OH, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy, in particularselected from halogen, C₁-C₂-alkyl, C₁-C₂-halogenalkyl, C₁-C₂-alkoxy andC₁-C₂-halogenalkoxy, more specifically selected from halogen, such as F,Cl and Br.

According to one embodiment R^(3a) is independently selected fromhalogen, OH, CN, C₁-C₂-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyand C₁-C₂-halogenalkoxy. Specifically, R^(3a) is independently selectedfrom F, C, OH, CN, C₁-C₂-alkoxy, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-C₂-cyclopropyl andC₁-C₂-halogenalkoxy.

According to one embodiment R^(3a) is independently selected fromhalogen, such as F, Cl, Br and I, more specifically F, Cl and Br.

According to still another embodiment of formula I, R^(3a) isindependently selected from OH, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyand C₁-C₂-halogenalkoxy. Specifically, R^(3a) is independently selectedfrom OH, cyclopropyl and C₁-C₂-halogenalkoxy.

According to still another embodiment of formula I, R^(3a) isindependently selected from aryl and phenoxy, wherein the aryl andphenoxy group is unsubstituted or substituted with R^(33a) selected fromthe group consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy, in particular selected fromhalogen, C₁-C₂-alkyl, C₁-C₂-halogenalkyl, C₁-C₂-alkoxy andC₁-C₂-halogenalkoxy, more specifically selected from halogen, such as F,Cl and Br.

R^(3b) are the possible substituents for the carbocyclic, heteroaryl andaryl moieties of R³.

R^(3b) according to the invention is independently selected fromhalogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalky, C₁-C₄-halogenalkoxy andC₁-C₆-alkylthio;

According to one embodiment thereof R³ is independently selected fromhalogen, CN, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.Specifically, R^(3b) is independently selected from F, C, Br, OH, CN,CH₃, OCH₃, CHF₂, OCHF₂, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl1,1-F₂-cyclopropyl, 1,1-CO₂-cyclopropyl, OCF₃, and OCHF₂.

According to still another embodiment thereof R^(3b) is independentlyselected from halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.Specifically, R³ is independently selected from halogen, OH, CH₃, OCH₃,CN, CHF₂, OCHF₂, OCF₃, OCH₃, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl andhalogenmethoxy, more specifically independently selected from F, C, OH,CH₃, OCH₃, CHF₂, OCH₃, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl,1,1-F₂-cyclopropyl, 1,1-C₂-cyclopropyl, OCHF₂ and OCF₃.

Particularly preferred embodiments of R³ according to the invention arein Table P3 below, wherein each line of lines P3-1 to P3-16 correspondsto one particular embodiment of the invention. Thereby, for every R³that is present in the inventive compounds, these specific embodimentsand preferences apply independently of the meaning of any other R³ thatmay be present in the ring:

TABLE P3 No. R³ P3-1 H P3-2 Cl P3-3 F P3-4 Br P3-5 OH P3-6 CN P3-7 NO₂P3-8 CH₃ P3-9 CH₂CH₃ P3-10 CF₃ P3-11 CHF₂ P3-12 OCH₃ P3-13 OCH₂CH₃ P3-14OCF₃ P3-15 OCHF₂ P3-16 NH-TsR⁴ according to the invention is in each case independently selectedfrom hydrogen, halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, five- or six-memberedheteroaryl and aryl; wherein the heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein

-   R^(x) is C₁-C₄-alkyl, C₁-C₄-halogenalkyl, unsubstituted aryl or aryl    that is substituted with one, two, three, four or five substituents    R^(x4) independently selected from C₁-C₄-alkyl, halogen, OH, CN,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    wherein the acyclic moieties of R⁴ are unsubstituted or substituted    with identical or different groups R^(4a) which independently of one    another are selected from:    R^(4a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalky, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl    and phenoxy, wherein the aryl and phenoxy group is unsubstituted or    substituted with R^(41a) selected from the group consisting of    halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and    C₁-C₄-halogenalkoxy;    wherein the carbocyclic, heteroaryl and aryl moieties of R⁴ are    unsubstituted or substituted with identical or different groups    R^(4b) which independently of one another are selected from:    R^(4b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalky,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

For every R⁴ that is present in the inventive compounds, the followingembodiments and preferences apply independently of the meaning of theother R⁴ that may be present in the ring.

According to one embodiment of formula I, R⁴ is H, halogen orC₁-C₆-alkyl, in particular H, CH₃, Et, F, C, more specifically H, CH₃, For Cl most preferred H, F or Cl.

According to another of formula I, R⁴ is halogen, in particular Br, F orC, more specifically F or Cl.

According to another embodiment of formula I, R⁴ is F

According to another embodiment of formula I, R⁴ is Cl

According to another embodiment of formula I, R⁴ is Br.

According to still another embodiment of formula I, R⁴ is hydrogen.

According to still another embodiment of formula I, R⁴ is OH.

According to still another embodiment of formula I, R⁴ is CN.

According to still another embodiment of formula I, R⁴ is NO₂.

According to still another embodiment of formula I, R⁴ is SH.

In a further specific embodiment R⁴ is NH₂, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂ or NH—SO₂—R^(x), wherein R^(x) is C₁-C₄-alkyl,C₁-C₄-halogenalkyl, unsubstituted phenoxy or aryl that is substitutedwith one, two, three, four or five substituents R^(x4) independentlyselected from C₁-C₄-alkyl, halogen, OH, CN, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, or C₁-C₄-halogenalkoxy. In particular C₁-C₄-alkyl, such asNHCH₃ and N(CH₃)₂. In particular R^(x) is C₁-C₄-alkyl, and phenyl thatis substituted with one CH₃, more specifically SO₂—R^(x) is CH₃ andtosyl group (“Ts”).

According to still another embodiment of formula I, R⁴ is C₁-C₆-alkyl,in particular C₁-C₄-alkyl, such as CH₃ or CH₂CH₃.

According to still another embodiment of formula I, R⁴ isC₁-C₆-halogenalkyl, in particular C₁-C₄-halogenalkyl, such as CF₃, CHF₂,CH₂F, CCl₃, CHCl₂, CH₂Cl, CF₃CH₂, CCl₃CH₂ or CF₂CHF₂.

According to still a further embodiment, R⁴ is C₂-C₆-alkenyl orC₂-C₆-halogenalkenyl, in particular C₂-C₄-alkenyl orC₂-C₄-halogenalkenyl, such as CH═CH₂, CH═CCl₂, CH═CF₂, CCl═CCl₂, CF═CF₂,CH═CH₂, CH₂CH═CCl₂, CH₂CH═CF₂, CH₂CCl═CCl₂, CH₂CF═CF₂, CCl₂CH═CCl₂,CF₂CH═CF₂, CCl₂CCl═CCl₂, or CF₂CF═CF₂.

According to still a further embodiment, R⁴ is C₂-C₆-alkynyl orC₂-C₆-halogenalkynyl, in particular C₂-C₄-alkynyl orC₂-C₄-halogenalkynyl, such as C≡CH, C≡CCl, C≡CF. CH₂C≡CH, CH₂C≡CCl, orCH₂C≡CF.

According to still another embodiment of formula I, R⁴ is C₁-C₆-alkoxy,in particular C₁-C₄-alkoxy, more specifically C₁-C₂-alkoxy such as OCH₃or OCH₂CH₃.

According to still another embodiment of formula I, R⁴ isC₁-C₆-halogenalkoxy, in particular C₁-C₄-halogenalkoxy, morespecifically C₁-C₂-halogenalkoxy such as OCF₃, OCHF₂, OCH₂F, OCCl₃,OCHCl₂ or OCH₂Cl, in particular OCF₃, OCHF₂, OCCl₃ or OCHCl₂.

In a further specific embodiment R⁴ is C₃-C₆-cycloalkyl, in particularcyclopropyl.

In a further specific embodiment, R⁴ is C₃-C₆-cycloalkyl, for examplecyclopropyl, substituted with one, two, three or up to the maximumpossible number of identical or different groups R^(4b) as defined andpreferably herein.

According to still another embodiment of formula I, R⁴ isC₃-C₆-halogencycloalkyl. In a special embodiment R⁴ is fully orpartially halogenated cyclopropyl.

According to still another embodiment of formula I, R⁴ is unsubstitutedaryl or aryl that is substituted with one, two, three or four R^(4b), asdefined herein. In particular, R⁴ is unsubstituted phenyl or phenyl thatis substituted with one, two, three or four R^(4b), as defined herein.

According to still another embodiment of formula I, R⁴ is unsubstituted5- or 6-membered heteroaryl. According to still a further embodiment, R⁴is 5- or 6-membered heteroaryl that is substituted with one, two orthree R^(4b), as defined herein.

According to still another embodiment of formula I, R⁴ is in each caseindependently selected from hydrogen, halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy and C₃-C₆-cycloalkyl; whereinthe acyclic moieties of R⁴ are not further substituted or carry one,two, three, four or five identical or different groups R⁴ as definedbelow and wherein the cycloalkyl moieties of R⁴ are not furthersubstituted or carry one, two, three, four or five identical ordifferent groups R^(4b) as defined below.

According to still another embodiment of formula I, R⁴ is independentlyselected from hydrogen, halogen, CN, OH, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, wherein the acyclic andcyclic moieties of R⁴ are unsubstituted or substituted by halogen.

According to still another embodiment of formula I, R⁴ is independentlyselected from hydrogen, halogen, OH, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₁-C₆-alkoxy and C₁-C₆-halogenalkoxy, in particular independentlyselected from H, F, Cl, Br, CN, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy.

According to still another embodiment of formula I, R⁴ is independentlyselected from H, CN, halogen or C₁-C₆-alkyl, in particular H, CN, CH₃,Et, F, Cl, more specifically H, CN, CH₃, F or C most preferred H, CH₃, For Cl.

R^(4a) are the possible substituents for the acyclic moieties of R⁴.

R^(4a) according to the invention is independently selected fromhalogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalky,C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl and phenoxy, wherein the aryland phenoxy group is unsubstituted or substituted with R^(44a) selectedfrom the group consisting of halogen, OH, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy, in particularselected from halogen, C₁-C₂-alkyl, C₁-C₂-halogenalkyl, C₁-C₂-alkoxy andC₁-C₂-halogenalkoxy, more specifically selected from halogen, such as F,Cl and Br.

According to one embodiment R^(4a) is independently selected fromhalogen, OH, CN, C₁-C₂-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyand C₁-C₂-halogenalkoxy. Specifically, R^(4a) is independently selectedfrom F, C, OH, CN, C₁-C₂-alkoxy, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl andC₁-C₂-halogenalkoxy.

According to one embodiment R^(4a) is independently selected fromhalogen, such as F, Cl, Br and I, more specifically F, Cl and Br.

According to still another embodiment of formula I, R^(4a) isindependently selected from OH, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyand C₁-C₂-halogenalkoxy. Specifically, R^(4a) is independently selectedfrom OH, cyclopropyl and C₁-C₂-halogenalkoxy.

According to still another embodiment of formula I, R^(4a) isindependently selected from aryl and phenoxy, wherein the aryl andphenoxy group is unsubstituted or substituted with R^(44a) selected fromthe group consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy, in particular selected fromhalogen, C₁-C₂-alkyl, C₁-C₂-halogenalkyl, C₁-C₂-alkoxy andC₁-C₂-halogenalkoxy, more specifically selected from halogen, such as F,Cl and Br.

R^(4b) are the possible substituents for the carbocyclic, heteroaryl andaryl moieties of R⁴.

R⁴ according to the invention is independently selected from halogen,OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalky, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio;

According to one embodiment thereof R⁴ is independently selected fromhalogen, CN, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.Specifically, R⁴ is independently selected from F, C, Br, OH, CN, CH₃,OCH₃, CHF₂, OCHF₂, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl1,1-F₂-cyclopropyl, 1,1-CO₂-cyclopropyl, OCF₃, and OCHF₂.

According to still another embodiment thereof R^(4b) is independentlyselected from halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.Specifically, R⁴ is independently selected from halogen, OH, CH₃, OCH₃,CN, CHF₂, OCHF₂, OCF₃, OCH₃, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl andhalogenmethoxy, more specifically independently selected from F, C, OH,CH₃, OCH₃, CHF₂, OCH₃ cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl,1,1-F₂-cyclopropyl, 1,1-C₂-cyclopropyl, OCHF₂ and OCF₃.

Particularly preferred embodiments of R⁴ according to the invention arein Table P4 below, wherein each line of lines P4-1 to P4-16 correspondsto one particular embodiment of the invention. Thereby, for every R⁴that is present in the inventive compounds, these specific embodimentsand preferences apply independently of the meaning of any other R⁴ thatmay be present in the ring:

TABLE P4 “Ts” in the table stands for the tosylgroup SO₂-(p-CH₃)phenyl.No. R⁴ P4-1 H P4-2 Cl P4-3 F P4-4 Br P4-5 OH P4-6 CN P4-7 NO₂ P4-8 CH₃P4-9 CH₂CH₃ P4-10 CF₃ P4-11 CHF₂ P4-12 OCH₃ P4-13 OCH₂CH₃ P4-14 OCF₃P4-15 OCHF₂ P4-16 NH-Ts

Y according to the invention is O or S(O)_(m), wherein m is 0, 1 or 2.

According to one embodiment of formula I, Y is O.

According to another embodiment of formula I, Y is S.

According to another embodiment of formula I, Y is SO.

According to another embodiment of formula I, Y is SO₂.

Z according to the invention is N or CR⁵.

Z according to the invention is N

Z according to the invention is CR⁵.

R⁵ according to the invention is in each case independently selectedfrom is are independently selected from H, halogen, OH, CN, NO₂, SH,NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), CH(═O), C(═O)C₁-C₆-alkyl,C(═O)NH(C₁-C₆-alkyl), CR′═NOR″, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, S(O)_(m)—C₁-C₆-alkyl, three-, four-, five- orsix-membered saturated or partially unsaturated heterocycle, five- orsix-membered heteroaryl and phenyl; wherein the heterocycle orheteroaryl contains one, two or three heteroatoms selected from N, O andS; and wherein R′ and R″ are independently unsubstituted or substitutedby R′″ which is independently selected from halogen, OH, CN, NO₂, SH,NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl,C₂-C₆-halogenalkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and phenyl; wherein m is 0, 1and 2;

-   R^(x) is C₁-C₄-alkyl, C₁-C₄-halogenalkyl, unsubstituted aryl or aryl    that is substituted with one, two, three, four or five substituents    R⁵ independently selected from C₁-C₄-alkyl, halogen, OH, CN,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    and wherein the aliphatic moieties of R⁵ are not further substituted    or carry 1, 2, 3 or up to the maximum possible number of identical    or different groups R^(5a) which independently of one another are    selected from:-   R^(5a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,    C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    five- or six-membered heteroaryl, phenyl and phenoxy, wherein the    heteroaryl, phenyl and phenoxy group is unsubstituted or    unsubstituted or substituted with R^(51a) selected from the group    consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    wherein the alicyclic, phenyl, heterocyclic and heteroaryl moieties    of R⁵ are unsubstituted or substituted with identical or different    groups R^(5b) which independently of one another are selected from:-   R^(5b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy, and C₁-C₆-alkylthio;

According to one specific embodiment, R⁵ is H.

According to one specific embodiment, R⁵ is halogen, in particular F, C,Br or I, more specifically F, Cl or Br, in particular F or Cl.

According to still another embodiment of formula I, R⁵ is F.

According to still another embodiment of formula I, R⁵ is Cl.

According to still another embodiment of formula I, R⁵ is Br.

According to a further specific embodiment, R⁵ is OH.

According to a further specific embodiment, R⁵ is CN.

According to a further specific embodiment, R⁵ is NO₂.

According to still another embodiment of formula I, R⁵ is SH.

According to still another embodiment of formula I, R⁵ is NH₂.

According to still another embodiment of formula I, R is,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)(C₁-C₄-alkyl),N(C(═O)(C₁-C₄-alkyl)₂, wherein C₁-C₄-alkyl is CH₃, C₂H₅, n-propyl,i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R⁵ isNH—SO₂—R^(x) such as NH—SO₂—CH₃, NH—SO₂—CH₂—CH₃, NH—SO₂—CF₃ orNH—SO₂-Ts.

According to a further specific embodiment of formula I, R⁵ is CH(═O),C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl) or C(═O)NH(C₁-C₆-alkyl), whereinalkyl is CH₃, C₂H₅, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl,n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R⁵ is CR′═NOR″such as C(CH₃)═NOCH₃, C(CH₃)═NOCH₂CH₃ or C(CH₃)═NOCF₃.

According to a further specific embodiment, R⁵ is C₁-C₆-alkyl, inparticular C₁-C₄-alkyl, such as CH₃, C₂H₅, n-propyl, i-propyl, n-butyl,i-butyl, tert-butyl, n-pentyl or i-pentyl, in particular CH₃.

According to a further specific embodiment, R⁵ is C₁-C₆-halogenalkyl, inparticular C₁-C₄-halogenalkyl, such as CF₃, CCl₃, FCH₂, ClCH₂, F₂CH,C₂CH, CF₃CH₂, CCl₃CH₂ or CF₂CHF₂.

According to still a further embodiment, R⁵ is C₂-C₆-alkenyl, inparticular C₂-C₄-alkenyl, such as CH═CH₂ or CH₂, CH═CH₂.

According to still another embodiment of formula I R⁵ isC₃-C₆-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I, R⁵ isC₃-C₆-halogencycloalkyl. In a special embodiment R¹ is fully orpartially halogenated cyclopropyl.

According to still a further embodiment, R⁵ isC₃-C₆-cycloalkyl-C₂-C₆-alkenyl, in particularC₃-C₆-cycloalkyl-C₂-C₄-alkenyl, more specificallyC₃-C₆-cycloalkyl-C₂-C₃-alkenyl, such as C₃H₅—CH═CH₂.

According to a further specific embodiment, R⁵ is C₂-C₆-halogenalkenyl,in particular C₂-C₄-halogenalkenyl, more specificallyC₂-C₃-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF₂, CH═CCl₂,CH₂CH═CHF, CH₂CH═CHCl, CH₂CH═CF₂, CH₂CH═CCl₂. CH₂CF═CF₂, CH₂CCl═CCl₂.

CF₂CF═CF₂ or CCl₂CCl═CCl₂.

According to still a further embodiment, R⁵ is C₂-C₆-alkynyl, inparticular C₂-C₄-alkynyl, more specifically C₂-C₃-alkynyl, such as C≡CH.

According to still a further embodiment, R⁵ is C₂-C₆-halogenalkynyl, inparticular C₂-C₄-halogenalkynyl, more specifically C₂-C₃-halogenalkynyl.

According to a further specific embodiment, R⁵ is C₁-C₆-alkoxy, inparticular C₁-C₄-alkoxy, more specifically C₁-C₂-alkoxy such as OCH₃ orOCH₂CH₃.

According to a further specific embodiment, R⁵ is C₁-C₆-halogenalkoxy,in particular C₁-C₄-halogenalkoxy, more specifically C₁-C₂-halogenalkoxysuch as OCF₃, OCHF₂, OCH₂F, OCCl₃, OCHCl₂, OCH₂Cl and OCF₂CHF₂, inparticular OCF₃, OCHF₂ and OCF₂CHF₂.

According to a further specific embodiment of formula I, R⁵ isC₂-C₆-alkenyloxy, in particular C₂-C₄-alkenyloxy, more specificallyC₁-C₂-alkenyloxy such as OCH═CH₂, OCH₂CH═CH₂.

According to a further specific embodiment of formula I, R⁵ isC₂-C₆-alkynyloxy, in particular C₂-C₄-alkynyloxy, more specificallyC₁-C₂-alkynyloxy such as OC≡CH

According to a further specific embodiment of formula I, R⁵ isS(O)_(m)—C₁-C₆-alkyl, wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and m is 1, 2 or 3.

According to a further specific embodiment of formula I, R⁵ isS(O)_(m)—C₁-C₆-halogenalkyl, wherein halogenalkyl is CF₃ or CHF₂ and mis 1, 2 or 3.

According to still another embodiment of formula I, R⁵ is a partiallyunsaturated three-, four-, five-, six-, seven-, eight-, nine-, orten-membered heterocycle, in particular three-, four-, five- orsix-membered, wherein the heterocycle contains one, two, three or fourheteroatoms selected from N, O and S, and wherein the heterocycle isunsubstituted or substituted by substituents R^(5b) as defined below.According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, R⁵ is a saturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedheterocycle, in particular three-, four-, five- or six-membered, whereinthe heterocycle contains one, two, three or four heteroatoms selectedfrom N, O and S, and wherein the heterocycle is unsubstituted orsubstituted by substituents R^(5b) as defined below. According to oneembodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, in the embodimentsof R⁵ described above, the heterocycle contains preferably one, two orthree, more specifically one or two heteroatoms selected from N, O andS. More specifically, the hetereocycle contains one heteroatom selectedfrom N, O and S. In particular, the heterocycle contains one or two, inparticular one O.

According to one embodiment, R⁵ is a 4-membered saturated heterocyclewhich contains 1 or 2 heteroatoms, in particular 1 heteroatom, from thegroup consisting of N, O and S, as ring members.

According to one embodiment, the heterocycle contains one O asheteroatom. For example, the formed heterocycle is oxetane. According toone embodiment thereof, the heterocycle is unsubstituted, i.e. it doesnot carry any substituent R^(5b). According to still another embodimentof formula I, it is substituted by R⁵.

According to still another embodiment of formula I, R⁵ is a 5-memberedsaturated heterocycle which contains 1, 2 or 3, in particular 1 or 2,heteroatoms from the group consisting of N, O and S, as ring members.According to one embodiment, the heterocycle contains one O asheteroatom.

According to one embodiment thereof, the heterocycle is unsubstituted,i.e. it does not carry any substituent R^(5b). According to stillanother embodiment of formula I, it is substituted by R^(5b).

According to still another embodiment of formula I, R⁵ is a 6-memberedsaturated heterocycle which contains 1, 2 or 3, in particular 1 or 2,heteroatoms from the group consisting of N, O and S as ring members.According to one embodiment thereof, the heterocycle is unsubstituted,i.e. it does not carry any substituent R^(5b). According to stillanother embodiment of formula I, it is substituted by R^(5b). Accordingto one specific embodiment thereof, said 6-membered saturatedheterocycle contains 1 or 2, in particular 1, heteroatom(s) O. Accordingto one embodiment thereof, the respective 6-membered heterocycle isunsubstituted, i.e. it does not carry any substituent R⁵. According tostill another embodiment of formula I, it is substituted by R⁵.

According to still another embodiment of formula I, R⁵ isphenyl-C₁-C₆-alkyl, such as phenyl-CH₂, wherein the phenyl moiety ineach case is unsubstituted or substituted by one, two or three identicalor different groups R^(5b) which independently of one another areselected from halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl andC₁-C₂-halogenalkoxy, in particular CN, F, Cl, Br, CH₃, OCH₃, CHF₂, CF₃,OCHF₂, and OCF₃.

According to still a further specific embodiment, R⁵ is unsubstitutedphenyl or phenyl that is substituted by one, two, three or four R^(5b),as defined and preferably herein. In particular, R⁵ is unsubstitutedphenyl or phenyl that is substituted by one, two, three or four R^(5b),as defined herein. In one embodiment R⁵ is unsubstituted phenyl.

According to still another embodiment of formula I, R⁵ is a 5-memberedheteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl,thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl,pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl,imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl,isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl,1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.

According to still another embodiment of formula I, R⁵ is a 6-memberedheteroaryl, such as pyri-din-2-yl, pyridin-3-yl, pyridin-4-yl,pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and1,2,4-triazin-3-yl.

According to one further embodiment, R⁵ is in each case independentlyselected from halogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl,S(O)_(m)—C₁-C₆-alkyl, three-, four-, five- or six-membered saturated orpartially unsaturated heterocycle, five- or six-membered heteroaryl andphenyl; wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the acyclic moietiesof R⁵ are not further substituted or carry one, two, three or up to themaximum possible number of identical or different groups R^(5a) asdefined and preferably defined herein, and wherein the heterocyclic,alicyclic, phenyl and heteroaryl moieties of R⁵ are not furthersubstituted or carry one, two, three, four, five or up to the maximumnumber of identical or different groups R^(5b) as defined and preferablydefined herein.

According to one further embodiment, R⁵ is in each case independentlyselected from halogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy,C₃-C₆-cycloalkyl, S(O)_(m)—C₁-C₆-alkyl, three-, four-, five- orsix-membered saturated or partially unsaturated heterocycle, five- orsix-membered heteroaryl and phenyl; wherein the heterocycle orheteroaryl contains one, two or three heteroatoms selected from N, O andS; and wherein the acyclic moieties of R⁵ are not further substituted orcarry one, two, three or up to the maximum possible number of identicalor different groups R^(5a) as defined and preferably defined herein, andwherein the heterocyclic, alicyclic, phenyl and heteroaryl moieties ofR⁵ are not further substituted or carry one, two, three, four, five orup to the maximum number of identical or different groups R^(5b) asdefined and preferably defined herein. According to one specificembodiment, the acyclic and cyclic moieties of R⁵ are not furthersubstituted, according to another embodiment, the acyclic moieties of R⁵carry one, two, three or four identical or different groups R^(5a) asdefined and preferably defined herein.

According to a further embodiment, R⁵ is in each case independentlyselected from halogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl andS(O)_(m)—C₁-C₆-alkyl, wherein the acyclic moieties of R⁵ are not furthersubstituted or carry one, two, three or up to the maximum possiblenumber of identical or different groups R^(5a) as defined and preferablydefined herein, and wherein the cycloalkyl moieties of R⁵ are notfurther substituted or carry one, two, three, four, five or up to themaximum number of identical or different groups R^(5b) as defined andpreferably defined herein.

According to a further embodiment, R⁵ is in each case independentlyselected from halogen, CN, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl andS(O)_(m)—C₁-C₆-alkyl, wherein the acyclic moieties of R⁵ are not furthersubstituted or carry one, two, three or up to the maximum possiblenumber of identical or different groups R^(5a) as defined and preferablydefined herein, and wherein the cycloalkyl moieties of R⁵ are notfurther substituted or carry one, two, three, four, five or up to themaximum number of identical or different groups R^(5b) as defined andpreferably defined herein. According to one specific embodiment, theacyclic and cyclic moieties of R⁵ are not further substituted, accordingto another embodiment, the acyclic moieties of R⁵ carry one, two, threeor four identical or different groups R^(5a) as defined and preferablydefined herein.

According to still a further embodiment, R⁵ is in each caseindependently selected from halogen, C₁-C₆-alkyl and C₁-C₆-alkoxy,wherein the acyclic moieties of R⁵ are not further substituted or carryone, two, three or up to the maximum possible number of identical ordifferent groups R^(5a) defined and preferably defined herein.

According to still a further embodiment, R⁵ is in each caseindependently selected from CN, halogen, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₁-C₆-alkoxy and C₁-C₆-halogenalkoxy, wherein theacyclic moieties of R⁵ are not further substituted or carry one, two,three or up to the maximum possible number of identical or differentgroups R^(5a) defined and preferably defined herein. According to onespecific embodiment, the acyclic and cyclic moieties of R⁵ are notfurther substituted, according to another embodiment, the acyclicmoieties of R⁵ carry one, two, three or four identical or differentgroups R^(5a) as defined and preferably defined herein.

According to still a further embodiment, R⁵ is in each caseindependently selected from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy or CN.

R^(5a) are the possible substituents for the acyclic moieties of R⁵.R^(5a) is independently selected from halogen, OH, CN, C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, five-or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryland phenyl group is unsubstituted or carries one, two, three, four orfive substituents R^(5a) selected from the group consisting of halogen,OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy.

According to one embodiment R^(5a) is independently selected fromhalogen, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl andC₁-C₄-halogenalkoxy. Specifically, R^(5a) is independently selected fromF, C, Br, I, C₁-C₂-alkoxy, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl andC₁-C₂-halogenalkoxy.

According to a further embodiment, R^(5a) is independently halogen, inparticular selected from F, Cl, Br and I, more specifically F, Cl andBr.

R^(5b) are the possible substituents for the cycloalkyl, heterocycle,heteroaryl and phenyl moieties of R⁵. R^(5b) according to the inventionis independently selected from halogen, OH, CN, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

According to one embodiment thereof R^(5b) is independently selectedfrom halogen, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl andC₁-C₄-halogenalkoxy, in particular halogen, C₁-C₄-alkyl andC₁-C₄-alkoxy. Specifically, R^(5b) is independently selected from F, Cl,CN, CH₃, OCH₃ and halogenmethoxy.

Particularly preferred embodiments of R⁵ according to the invention arein Table P5 below, wherein each line of lines P5-1 to P5-34 correspondsto one particular embodiment of the invention, wherein P5-1 to P5-34 arealso in any combination with one another a preferred embodiment of thepresent invention:

TABLE P5 No. R⁵ P5-1 H P5-2 Cl P5-3 F P5-4 Br P5-5 OH P5-6 CN P5-7 NO₂P5-8 CH₃ P5-9 CH₂CH₃ P5-10 cPr P5-11 CF₃ P5-12 CHF₂ P5-13 CH₂F P5-14CCl₃ P5-15 CHCl₂ P5-16 CH₂Cl P5-17 CH₂CF₂₃ P5-18 CH₂CCl₃ P5-19 CHF₂CF₂P5-20 OCH₃ P5-21 OCH₂CH₃ P5-22 OCF₃ P5-23 OCHF₂ P5-24 OCH₂F P5-25OCF₂CHF₂ P5-26 OCCl₃ P5-27 OCHCl₂ P5-28 OCH₂Cl P5-29 CCH P5-30 OCΞCHP5-31 CH═CH₂ P5-32 OCH═CH₂ P5-33 OCH₂CH═CH₂ P5-34 S(O)₂—CH₃

n according to the invention is 0, 1, or 2.

According to one specific embodiment, n is 0.

According to one specific embodiment, n is 1.

According to one specific embodiment, n is 2.

X according to the invention is in each case independently selected fromhalogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), CH(═O),C(═O)C₁-C₆-alkyl, C(═O)NH(C₁-C₆-alkyl), CR′═NOR″, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₁-C₆-halogenalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, S(O)_(m)—C₁-C₆-alkyl, three-,four-, five- or six-membered saturated or partially unsaturatedheterocycle, five- or six-membered heteroaryl and phenyl; wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; and wherein R′ and R″ are independentlyunsubstituted or substituted by R′″ which is independently selected fromhalogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl, C₁-C₆-alkoxy,C₁-C₆-halogenalkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl andphenyl.

and wherein the aliphatic moieties of X are not further substituted orcarry 1, 2, 3 or up to the maximum possible number of identical ordifferent groups X^(a) which independently of one another are selectedfrom:

-   X^(a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,    C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    five- or six-membered heteroaryl, phenyl and phenoxy, wherein the    heteroaryl, phenyl and phenoxy group is unsubstituted or    unsubstituted or substituted with X^(a) selected from the group    consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;    wherein the alicyclic, phenyl, heterocyclic and heteroaryl moieties    of X are unsubstituted or substituted with identical or different    groups X^(b) which independently of one another are selected from:-   X^(b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy, and C₁-C₆-alkylthio;

According to one specific embodiment, X is halogen, in particular F, C,Br or I, more specifically F, Cl or Br, in particular F or Cl.

According to still another embodiment of formula I, X is F.

According to still another embodiment of formula I, X is Cl.

According to still another embodiment of formula I, X is Br.

According to a further specific embodiment, X is OH.

According to a further specific embodiment, X is CN.

According to a further specific embodiment, X is NO₂.

According to still another embodiment of formula I, X is SH.

According to still another embodiment of formula I, X is NH₂.

According to still another embodiment of formula I, X is,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂. NH(C(═O)(C₁-C₄-alkyl),N(C(═O)(C₁-C₄-alkyl)₂, wherein C₁-C₄-alkyl is CH₃, C₂H₅, n-propyl,i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, X isNH—SO₂—R^(x) such as NH—SO₂—CH₃, NH—SO₂—CH₂—CH₃, NH—SO₂—CF₃ orNH—SO₂-Ts.

According to a further specific embodiment of formula I, X is CH(═O),C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl) or C(═O)NH(C₁-C₆-alkyl), whereinalkyl is CH₃, C₂H₅, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl,n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, X is CR′═NOR″such as C(CH₃)═NOCH₃, C(CH₃)═NOCH₂CH₃ or C(CH₃)═NOCF₃.

According to a further specific embodiment, X is C₁-C₆-alkyl, inparticular C₁-C₄-alkyl, such as CH₃, C₂H₅, n-propyl, i-propyl, n-butyl,i-butyl, tert-butyl, n-pentyl or i-pentyl, in particular CH₃.

According to a further specific embodiment, X is C₁-C₆-halogenalkyl, inparticular C₁-C₄-halogenalkyl, such as CF₃, CCl₃, FCH₂, ClCH₂, F₂CH,C₂CH, CF₃CH₂, CCl₃CH₂ or CF₂CHF₂.

According to still a further embodiment, X is C₂-C₆-alkenyl, inparticular C₂-C₄-alkenyl, such as CH═CH₂ or CH₂, CH═CH₂.

According to still another embodiment of formula I X isC₃-C₆-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I, X isC₃-C₆-halogencycloalkyl. In a special embodiment R¹ is fully orpartially halogenated cyclopropyl.

According to still a further embodiment, X isC₃-C₆-cycloalkyl-C₂-C₆-alkenyl, in particularC₃-C₆-cycloalkyl-C₂-C₄-alkenyl, more specificallyC₃-C₆-cycloalkyl-C₂-C₃-alkenyl, such as C₃H₅—CH═CH₂.

According to a further specific embodiment, X is C₂-C₆-halogenalkenyl,in particular C₂-C₄-halogenalkenyl, more specificallyC₂-C₃-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF₂, CH═CCl₂,CH₂CH═CHF, CH₂CH═CHCl, CH₂CH═CF₂, CH₂CH═CCl₂. CH₂CF═CF₂, CH₂CCl═CCl₂.

CF₂CF═CF₂ or CCl₂CCl═CCl₂.

According to still a further embodiment, X is C₂-C₆-alkynyl, inparticular C₂-C₄-alkynyl, more specifically C₂-C₃-alkynyl, such as C≡CH.

According to still a further embodiment, X is C₂-C₆-halogenalkynyl, inparticular C₂-C₄-halogenalkynyl, more specifically C₂-C₃-halogenalkynyl.

According to a further specific embodiment, X is C₁-C₆-alkoxy, inparticular C₁-C₄-alkoxy, more specifically C₁-C₂-alkoxy such as OCH₃ orOCH₂CH₃.

According to a further specific embodiment, X is C₁-C₆-halogenalkoxy, inparticular C₁-C₄-halogenalkoxy, more specifically C₁-C₂-halogenalkoxysuch as OCF₃, OCHF₂, OCH₂F, OCCl₃, OCHCl₂, OCH₂Cl and OCF₂CHF₂, inparticular OCF₃, OCHF₂ and OCF₂CHF₂.

According to a further specific embodiment of formula I, X isC₂-C₆-alkenyloxy, in particular C₂-C₄-alkenyloxy, more specificallyC₁-C₂-alkenyloxy such as OCH═CH₂, OCH₂CH═CH₂.

According to a further specific embodiment of formula I, X isC₂-C₆-alkynyloxy, in particular C₂-C₄-alkynyloxy, more specificallyC₁-C₂-alkynyloxy such as OC≡CH

According to a further specific embodiment of formula I, X isS(O)_(m)—C₁-C₆-alkyl, wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and m is 1, 2 or 3.

According to a further specific embodiment of formula I, X isS(O)_(m)—C₁-C₆-halogenalkyl, wherein halogenalkyl is CF₃ or CHF₂ and mis 1, 2 or 3.

According to still another embodiment of formula I, X is a partiallyunsaturated three-, four-, five-, six-, seven-, eight-, nine-, orten-membered heterocycle, in particular three-, four-, five- orsix-membered, wherein the heterocycle contains one, two, three or fourheteroatoms selected from N, O and S, and wherein the heterocycle isunsubstituted or substituted by substituents X^(b) as defined below.According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, X is a saturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedheterocycle, in particular three-, four-, five- or six-membered, whereinthe heterocycle contains one, two, three or four heteroatoms selectedfrom N, O and S, and wherein the heterocycle is unsubstituted orsubstituted by substituents X^(b) as defined below. According to oneembodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, in the embodimentsof X described above, the heterocycle contains preferably one, two orthree, more specifically one or two heteroatoms selected from N, O andS. More specifically, the hetereocycle contains one heteroatom selectedfrom N, O and S. In particular, the heterocycle contains one or two, inparticular one O.

According to one embodiment, X is a 4-membered saturated heterocyclewhich contains 1 or 2 heteroatoms, in particular 1 heteroatom, from thegroup consisting of N, O and S, as ring members.

According to one embodiment, the heterocycle contains one O asheteroatom. For example, the formed heterocycle is oxetane. According toone embodiment thereof, the heterocycle is unsubstituted, i.e. it doesnot carry any substituent X^(b). According to still another embodimentof formula I, it is substituted by X^(b).

According to still another embodiment of formula I, X is a 5-memberedsaturated heterocycle which contains 1, 2 or 3, in particular 1 or 2,heteroatoms from the group consisting of N, O and S, as ring members.According to one embodiment, the heterocycle contains one O asheteroatom.

According to one embodiment thereof, the heterocycle is unsubstituted,i.e. it does not carry any substituent X^(b). According to still anotherembodiment of formula I, it is substituted by X^(b).

According to still another embodiment of formula I, X is a 6-memberedsaturated heterocycle which contains 1, 2 or 3, in particular 1 or 2,heteroatoms from the group consisting of N, O and S as ring members.According to one embodiment thereof, the heterocycle is unsubstituted,i.e. it does not carry any substituent X^(b). According to still anotherembodiment of formula I, it is substituted by X^(b). According to onespecific embodiment thereof, said 6-membered saturated heterocyclecontains 1 or 2, in particular 1, heteroatom(s) O. According to oneembodiment thereof, the respective 6-membered heterocycle isunsubstituted, i.e. it does not carry any substituent X^(b). Accordingto still another embodiment of formula I, it is substituted by X^(b).

According to still another embodiment of formula I, X isphenyl-C₁-C₆-alkyl, such as phenyl-CH₂, wherein the phenyl moiety ineach case is unsubstituted or substituted by one, two or three identicalor different groups X^(b) which independently of one another areselected from halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl andC₁-C₂-halogenalkoxy, in particular CN, F, Cl, Br, CH₃, OCH₃, CHF₂, CF₃,OCHF₂, and OCF₃.

According to still a further specific embodiment, X is unsubstitutedphenyl or phenyl that is substituted by one, two, three or four X^(b),as defined and preferably herein. In particular, X is unsubstitutedphenyl or phenyl that is substituted by one, two, three or four X^(b),as defined herein. In one embodiment X is unsubstituted phenyl.

According to still another embodiment of formula I, X is a 5-memberedheteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl,thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl,pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl,imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl,isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl,1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.

According to still another embodiment of formula I, X is a 6-memberedheteroaryl, such as pyri-din-2-yl, pyridin-3-yl, pyridin-4-yl,pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and1,2,4-triazin-3-yl.

According to one further embodiment, X is in each case independentlyselected from halogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl,S(O)_(m)—C₁-C₆-alkyl, three-, four-, five- or six-membered saturated orpartially unsaturated heterocycle, five- or six-membered heteroaryl andphenyl; wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the acyclic moietiesof X are not further substituted or carry one, two, three or up to themaximum possible number of identical or different groups X^(a) asdefined and preferably defined herein, and wherein the heterocyclic,alicyclic, phenyl and heteroaryl moieties of X are not furthersubstituted or carry one, two, three, four, five or up to the maximumnumber of identical or different groups X^(b) as defined and preferablydefined herein.

According to one further embodiment, X is in each case independentlyselected from halogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy,C₃-C₆-cycloalkyl, S(O)_(m)—C₁-C₆-alkyl, three-, four-, five- orsix-membered saturated or partially unsaturated heterocycle, five- orsix-membered heteroaryl and phenyl; wherein the heterocycle orheteroaryl contains one, two or three heteroatoms selected from N, O andS; and wherein the acyclic moieties of X are not further substituted orcarry one, two, three or up to the maximum possible number of identicalor different groups X^(a) as defined and preferably defined herein, andwherein the heterocyclic, alicyclic, phenyl and heteroaryl moieties of Xare not further substituted or carry one, two, three, four, five or upto the maximum number of identical or different groups X^(b) as definedand preferably defined herein. According to one specific embodiment, theacyclic and cyclic moieties of X are not further substituted, accordingto another embodiment, the acyclic moieties of X carry one, two, threeor four identical or different groups X^(a) as defined and preferablydefined herein.

According to a further embodiment, X is in each case independentlyselected from halogen, CN, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl andS(O)_(m)—C₁-C₆-alkyl, wherein the acyclic moieties of X are not furthersubstituted or carry one, two, three or up to the maximum possiblenumber of identical or different groups X^(a) as defined and preferablydefined herein, and wherein the cycloalkyl moieties of X are not furthersubstituted or carry one, two, three, four, five or up to the maximumnumber of identical or different groups X^(b) as defined and preferablydefined herein.

According to a further embodiment, X is in each case independentlyselected from halogen, CN, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl andS(O)_(m)—C₁-C₆-alkyl, wherein the acyclic moieties of X are not furthersubstituted or carry one, two, three or up to the maximum possiblenumber of identical or different groups X^(a) as defined and preferablydefined herein, and wherein the cycloalkyl moieties of X are not furthersubstituted or carry one, two, three, four, five or up to the maximumnumber of identical or different groups X^(b) as defined and preferablydefined herein. According to one specific embodiment, the acyclic andcyclic moieties of X are not further substituted, according to anotherembodiment, the acyclic moieties of X carry one, two, three or fouridentical or different groups X^(a) as defined and preferably definedherein.

According to still a further embodiment, X is in each case independentlyselected from halogen, C₁-C₆-alkyl and C₁-C₆-alkoxy, wherein the acyclicmoieties of X are not further substituted or carry one, two, three or upto the maximum possible number of identical or different groups X^(a)defined and preferably defined herein.

According to still a further embodiment, X is in each case independentlyselected from CN, halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxyand C₁-C₆-halogenalkoxy, wherein the acyclic moieties of X are notfurther substituted or carry one, two, three or up to the maximumpossible number of identical or different groups X^(a) defined andpreferably defined herein. According to one specific embodiment, theacyclic and cyclic moieties of X are not further substituted, accordingto another embodiment, the acyclic moieties of X carry one, two, threeor four identical or different groups X^(a) as defined and preferablydefined herein.

According to still a further embodiment, X is in each case independentlyselected from halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy,C₁-C₆-halogenalkoxy or CN.

X^(a) are the possible substituents for the acyclic moieties of X. X^(a)is independently selected from halogen, OH, CN, C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, five-or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryland phenyl group is unsubstituted or carries one, two, three, four orfive substituents X^(a′) selected from the group consisting of halogen,OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy.

According to one embodiment X^(a) is independently selected fromhalogen, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl andC₁-C₄-halogenalkoxy. Specifically, X^(a) is independently selected fromF, C, Br, I, C₁-C₂-alkoxy, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl andC₁-C₂-halogenalkoxy.

According to a further embodiment, X^(a) is independently halogen, inparticular selected from F, Cl, Br and I, more specifically F, Cl andBr.

X^(b) are the possible substituents for the cycloalkyl, heterocycle,heteroaryl and phenyl moieties of X. X^(b) according to the invention isindependently selected from halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

According to one embodiment thereof X is independently selected fromhalogen, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl andC₁-C₄-halogenalkoxy, in particular halogen, C₁-C₄-alkyl andC₁-C₄-alkoxy. Specifically, X^(b) is independently selected from F, Cl,CN, CH₃, OCH₃ and halogenmethoxy.

Particularly preferred embodiments of X according to the invention arein Table PX below, wherein each line of lines PX-1 to PX-33 correspondsto one particular embodiment of the invention, wherein PX-1 to PX-33 arealso in any combination with one another a preferred embodiment of thepresent invention:

TABLE PX No. X PX-1 Cl PX-2 F PX-3 Br PX-4 OH PX-5 CN PX-6 NO₂ PX-7 CH₃PX-8 CH₂CH₃ PX-9 cPr PX-10 CF₃ PX-11 CHF₂ PX-12 CH₂F PX-13 CCl₃ PX-14CHCl₂ PX-15 CH₂Cl PX-16 CH₂CF₂₃ PX-17 CH₂CCl₃ PX-18 CHF₂CF₂ PX-19 OCH₃PX-20 OCH₂CH₃ PX-21 OCF₃ PX-22 OCHF₂ PX-23 OCH₂F PX-24 OCF₂CHF₂ PX-25OCCl₃ PX-26 OCHCl₂ PX-27 OCH₂Cl PX-28 CCH PX-29 OCΞCH PX-30 CH═CH₂ PX-31OCH═CH₂ PX-32 OCH₂CH═CH₂ PX-33 S(O)₂—CH₃Q¹ according to the invention is in each case independently selectedfrom CN, halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, three-, four-, five- or six-memberedsaturated or partially unsaturated heterocycle, five- or six-memberedheteroaryl and aryl; wherein the heterocycle and heteroaryl containsone, two or three heteroatoms selected from N, O and S;wherein the aliphatic moieties of Q¹ are unsubstituted or substitutedwith identical or different groups Q^(a) which independently of oneanother are selected from:

-   Q^(a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    phenyl and phenoxy, wherein the phenyl and phenoxy group is    unsubstituted or carries 1, 2, 3, 4 or 5 substituents Q¹ selected    from the group consisting of halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy; and    wherein the cycloalkyl, heterocycle, heteroaryl and aryl moieties of    Q¹ are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the    maximum number of identical or different groups Q^(1b) which    independently of one another are selected from:-   Q^(1b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

According to a further specific embodiment, Q¹ is C₁-C₆-alkyl, inparticular C₁-C₄-alkyl, such as CH₃ or CH₂CH₃

According to a further specific embodiment, Q¹ is CN.

According to one specific embodiment, Q¹ is halogen, in particular F,Cl, Br or I, more specifically F, Cl or Br, in particular F or Cl.

According to still another embodiment of formula I, Q¹ is F.

According to still another embodiment of formula I, Q¹ is Cl.

According to a further specific embodiment, Q¹ is C₁-C₆-alkyl, inparticular C-alkyl, substituted by phenyl which carries 1, 2 or 3halogen.

According to a further specific embodiment, Q¹ is C₁-C₆-alkyl, inparticular C-alkyl, substituted by phenyl which is carries 1, 2 or 3C₁-C₄-alkoxy groups.

According to a further specific embodiment, Q¹ is C₁-C₆-alkyl, inparticular C-alkyl, substituted by phenyl which is carries 1, 2 or 3C₁-C₄-alkyl groups.

According to a further specific embodiment, Q¹ is C₁-C₆-alkyl, inparticular C-alkyl, substituted by phenyl which is carries 1, 2 or 3C₁-C₄-halogenalkyl groups.

According to a further specific embodiment, Q¹ is C₁-C₆-halogenalkyl, inparticular C₁-C₄-halogenalkyl, such as CF₃, CHF₂, CH₂F, CCl₃, CHCl₂ orCH₂Cl.

According to still a further embodiment, Q¹ is C₂-C₆-alkenyl orC₂-C₆-halogenalkenyl, in particular C₂-C₄-alkenyl orC₂-C₄-halogenalkenyl, such as CH═CH₂.

According to still a further embodiment, Q¹ is C₂-C₆-alkynyl orC₂-C₆-halogenalkynyl, in particular C₂-C₄-alkynyl orC₂-C₄-halogenalkynyl, such as C≡CH.

According to a further specific embodiment Q¹ is C₃-C₆-cycloalkyl, inparticular cyclopropyl.

In a further specific embodiment, Q¹ is C₃-C₆-cycloalkyl, for examplecyclopropyl, substituted by one, two, three or up to the maximumpossible number of identical or different groups Q^(b) as defined andpreferably herein.

According to a specific embodiment Q¹ is C₃-C₆-halogencycloalkyl. In aspecial embodiment Q¹ is fully or partially halogenated cyclopropyl.

According to a specific embodiment Q¹ is three-, four-, five- orsix-membered saturated or partially unsaturated heterocycle,

According to still another embodiment of formula I, Q¹ is a partiallyunsaturated three-, four-, five-, six-, seven-, eight-, nine-, orten-membered heterocycle, in particular three-, four-, five- orsix-membered, wherein the heterocycle contains one, two, three or fourheteroatoms selected from N, O and S, and wherein the heterocycle isunsubstituted or substituted by substituents Q^(1b) as defined below.According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, Q¹ is a saturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedheterocycle, in particular three-, four-, five- or six-membered, whereinthe heterocycle contains one, two, three or four heteroatoms selectedfrom N, O and S, and wherein the heterocycle is unsubstituted orsubstituted by substituents Q¹ as defined below. According to oneembodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, in the embodimentsof Q¹ described above, the heterocycle contains preferably one, two orthree, more specifically one or two heteroatoms selected from N, O andS. More specifically, the hetereocycle contains one heteroatom selectedfrom N, O and S. In particular, the heterocycle contains one or two, inparticular one O.

According to one embodiment, Q¹ is a 4-membered saturated heterocyclewhich contains 1 or 2 heteroatoms, in particular 1 heteroatom, from thegroup consisting of N, O and S, as ring members.

According to one embodiment, the heterocycle contains one O asheteroatom. For example, the formed heterocycle is oxetane. According toone embodiment thereof, the heterocycle is unsubstituted, i.e. it doesnot carry any substituent Q¹. According to still another embodiment offormula I, it is substituted by Q^(1b)

According to still another embodiment of formula I, Q¹ is a 5-memberedsaturated heterocycle which contains 1, 2 or 3, in particular 1 or 2,heteroatoms from the group consisting of N, O and S, as ring members.According to one embodiment, the heterocycle contains one O asheteroatom.

According to one embodiment thereof, the heterocycle is unsubstituted,i.e. it does not carry any substituent Q¹. According to still anotherembodiment of formula I, it is substituted by Q^(1b).

According to still a further specific embodiment, Q¹ is unsubstitutedaryl or aryl that is substituted by one, two, three or four Q^(1b), asdefined herein. In particular, Q¹ is unsubstituted phenyl or phenyl thatis substituted by one, two, three or four Q^(1b), as defined herein.

According to still a further specific embodiment, Q¹ is unsubstituted 5-or 6-membered heteroaryl. According to still a further embodiment, Q¹ is5- or 6-membered heteroaryl that is substituted by one, two or threeQ^(1b), as defined herein.

According to still a further specific embodiment, Q¹ is unsubstituted 5-or 6-membered heterocycle. According to still a further embodiment, Q¹is 5- or 6-membered heterocyle that is substituted by one, two or threeQ^(1b). as defined herein.

According to one further embodiment Q¹ according to the invention is ineach case independently selected from CN, halogen, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,five- or six-membered heteroaryl, aryl and benzyl; wherein theheteroaryl contains one, two or three heteroatoms selected from N, O andS; wherein Q^(1a) is selected from halogen, C₁-C₆-alkoxy,C₃-C₆-halogencycloalkyl, phenyl that is unsubstituted or substituted by1, 2, 3, 4 or 5 substituents Q^(11a) independently selected fromC₁-C₄-alkyl; and wherein the cycloalkyl moieties of Q¹ are not furthersubstituted or carry one, two, three, four or five identical ordifferent groups Q^(1b) as defined below.

According to a further embodiment, Q¹ is independently selected from CN,halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, in particular independentlyselected from hydrogen, C₁-C₄-alkyl and C₁-C₄-halogenalkyl.

Q^(1a) are the possible substituents for the aliphatic moieties of Q¹.

Q^(1a) according to the invention is independently selected fromhalogen, C₁-C₆-alkoxy, C₃-C₆-halogencycloalkyl, and phenyl, wherein thephenyl group is unsubstituted or carries one, two, three, four or fivesubstituents Q^(11a) selected from the group consisting of halogen, OH,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy,in particular selected from halogen, C₁-C₂-alkyl, C₁-C₂-halogenalkyl,C₁-C₂-alkoxy and C₁-C₂-halogenalkoxy, more specifically selected fromhalogen, such as F, Cl and Br.

According to one embodiment Q^(1a) is independently selected fromhalogen, OH, CN, C₁-C₂-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyland C₁-C₂-halogenalkoxy. Specifically, Q^(1a) is independently selectedfrom F, C, OH, CN, C₁-C₂-alkoxy, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl and C₁-C₂-halogenalkoxy.

According to one particular embodiment Q^(1a) is independently selectedfrom halogen, such as F, Cl, Br and I, more specifically F, Cl and Br.

According to a further embodiment, Q^(1a) is independently selected fromOH, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.Specifically, Q^(1a) is independently selected from OH, cyclopropyl andC₁-C₂-halogenalkoxy.

Q^(1b) are the possible substituents for the cycloalkyl, heteroaryl andaryl moieties of Q¹.

Q^(1b) according to the invention is independently selected fromhalogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₄-halogenalkoxy.

According to one embodiment thereof Q^(1b) is independently selectedfrom halogen, CN, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.Specifically, Q^(1b) is independently selected from F, C, OH, CN, CH₃,OCH₃ cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl and halogenmethoxy.

According to a further embodiment thereof Q^(1b) is independentlyselected from C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.

Specifically, Q^(1b) is independently selected from OH, CH₃, OCH₃cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl and halogenmethoxy, morespecifically independently selected from OH, CH₃, OCH₃ cyclopropyl,1-F-cyclopropyl, 1-Cl-cyclopropyl and OCHF₂.

Particularly preferred embodiments of Q¹ according to the invention arein Table Q1 below, wherein each line of lines Q1-1 to Q1-39 correspondsto one particular embodiment of the invention, wherein Q1-1 to Q1-39 arealso in any combination with one another a preferred embodiment of thepresent invention:

TABLE Q1 No. Q1 Q1-1 F Q1-2 Cl Q1-3 CN Q1-4 CH₃ Q1-5 CH₂CH₃ Q1-6 iPrQ1-7 cPr Q1-8 CF₃ Q1-9 CHF₂ Q1-10 CH₂F Q1-11 CCl₃ Q1-12 CHCl₂ Q1-13CH₂Cl Q1-14 CH₂CF₃ Q1-15 CH₂CCl₃ Q1-16 CHF₂CF₂ Q1-17 OCH₃ Q1-18 OCH₂CH₃Q1-19 OCF₃ Q1-20 OCHF₂ Q1-21 OCH₂F Q1-22 OCF₂CHF₂ Q1-23 OCCl₃ Q1-24OCHCl₂ Q1-25 OCH₂Cl Q1-26 CCH Q1-27 OC≡CH Q1-28 CH═CH₂ Q1-29 CH₂CH═CH₂Q1-30 OCH═CH₂ Q1-31 OCH₂CH═CH₂ Q1-32 Ph Q1-33 CH₂Ph Q1-34 3-py Q1-352-py Q1-36 4-py Q1-37

Q1-38

Q1-39

Q² according to the invention is in each case independently selectedfrom hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, three-, four-, five- or six-memberedsaturated or partially unsaturated heterocycle, five- or six-memberedheteroaryl and aryl; wherein the heterocycle and heteroaryl containsone, two or three heteroatoms selected from N, O and S;wherein the aliphatic moieties of Q² are unsubstituted or substitutedwith identical or different groups Q^(2a) which independently of oneanother are selected from:

-   Q^(2a) halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    phenyl and phenoxy, wherein the phenyl and phenoxy group is    unsubstituted or carries 1, 2, 3, 4 or 5 substituents Q^(22a)    selected from the group consisting of halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy; and    wherein the cycloalkyl, heterocycle, heteroaryl and aryl moieties of    Q² are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the    maximum number of identical or different groups Q^(2b) which    independently of one another are selected from:-   Q^(2b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

According to one specific embodiment, Q² is halogen, in particular F,Cl, Br or I, more specifically F, Cl or Br, in particular F or Cl.

According to still another embodiment of formula I, Q² is F.

According to still another embodiment of formula I, Q² is Cl.

According to a further specific embodiment, Q² is C₁-C₆-alkyl, inparticular C₁-C₄-alkyl, such as CH₃ or CH₂CH₃

According to a further specific embodiment, Q² is C₁-C₆-alkyl, inparticular C₁-alkyl, substituted by phenyl which is unsubstituted.

According to a further specific embodiment, Q² is C₁-C₆-alkyl, inparticular C₁-alkyl, substituted by phenyl which carries 1, 2 or 3halogen.

According to a further specific embodiment, Q² is C₁-C₆-alkyl, inparticular C₁-alkyl, substituted by phenyl which is carries 1, 2 or 3C₁-C₄-alkoxy groups.

According to a further specific embodiment, Q² is C₁-C₆-alkyl, inparticular C₁-alkyl, substituted by phenyl which is carries 1, 2 or 3C₁-C₄-alkyl groups.

According to a further specific embodiment, Q² is C₁-C₆-alkyl, inparticular C₁-alkyl, substituted by phenyl which is carries 1, 2 or 3C₁-C₄-halogenalkyl groups.

According to a further specific embodiment, Q² is C₁-C₆-halogenalkyl, inparticular C₁-C₄-halogenalkyl, such as CF₃, CHF₂, CH₂F, CCl₃, CHCl₂ orCH₂Cl.

According to still a further embodiment, Q² is C₂-C₆-alkenyl orC₂-C₆-halogenalkenyl, in particular C₂-C₄-alkenyl orC₂-C₄-halogenalkenyl, such as CH═CH₂.

According to still a further embodiment, Q² is C₂-C₆-alkynyl orC₂-C₆-halogenalkynyl, in particular C₂-C₄-alkynyl orC₂-C₄-halogenalkynyl, such as C≡CH.

According to a further specific embodiment Q² is C₃-C₆-cycloalkyl, inparticular cyclopropyl.

In a further specific embodiment, Q² is C₃-C₆-cycloalkyl, for examplecyclopropyl, substituted by one, two, three or up to the maximumpossible number of identical or different groups Q^(2b) as defined andpreferably herein.

According to a specific embodiment Q² is C₃-C₆-halogencycloalkyl. In aspecial embodiment Q² is fully or partially halogenated cyclopropyl.

According to a specific embodiment Q² is three-, four-, five- orsix-membered saturated or partially unsaturated heterocycle,

According to still another embodiment of formula I, Q² is a partiallyunsaturated three-, four-, five-, six-, seven-, eight-, nine-, orten-membered heterocycle, in particular three-, four-, five- orsix-membered, wherein the heterocycle contains one, two, three or fourheteroatoms selected from N, O and S, and wherein the heterocycle isunsubstituted or substituted by substituents Q^(2b) as defined below.According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, Q² is a saturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedheterocycle, in particular three-, four-, five- or six-membered, whereinthe heterocycle contains one, two, three or four heteroatoms selectedfrom N, O and S, and wherein the heterocycle is unsubstituted orsubstituted by substituents Q^(2b) as defined below. According to oneembodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, in the embodimentsof Q² described above, the heterocycle contains preferably one, two orthree, more specifically one or two heteroatoms selected from N, O andS. More specifically, the hetereocycle contains one heteroatom selectedfrom N, O and S. In particular, the heterocycle contains one or two, inparticular one O.

According to one embodiment, Q² is a 4-membered saturated heterocyclewhich contains 1 or 2 heteroatoms, in particular 1 heteroatom, from thegroup consisting of N, O and S, as ring members.

According to one embodiment, the heterocycle contains one O asheteroatom. For example, the formed heterocycle is oxetane. According toone embodiment thereof, the heterocycle is unsubstituted, i.e. it doesnot carry any substituent Q^(2b). According to still another embodimentof formula I, it is substituted by Q^(2b)

According to still another embodiment of formula I, Q² is a 5-memberedsaturated heterocycle which contains 1, 2 or 3, in particular 1 or 2,heteroatoms from the group consisting of N, O and S, as ring members.According to one embodiment, the heterocycle contains one O asheteroatom.

According to one embodiment thereof, the heterocycle is unsubstituted,i.e. it does not carry any substituent Q^(2b). According to stillanother embodiment of formula I, it is substituted by Q^(2b).

According to still a further specific embodiment, Q² is unsubstitutedaryl or aryl that is substituted by one, two, three or four Q^(2b), asdefined herein. In particular, Q² is unsubstituted phenyl or phenyl thatis substituted by one, two, three or four Q^(2b), as defined herein.

According to still a further specific embodiment, Q² is unsubstituted 5-or 6-membered heteroaryl. According to still a further embodiment, Q² is5- or 6-membered heteroaryl that is substituted by one, two or threeQ^(2b), as defined herein.

According to still a further specific embodiment, Q² is unsubstituted 5-or 6-membered heterocycle. According to still a further embodiment, Q²is 5- or 6-membered heterocyle that is substituted by one, two or threeQ^(2b). as defined herein.

According to one further embodiment Q² according to the invention is ineach case independently selected from hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,five- or six-membered heteroaryl, aryl and benzyl; wherein theheteroaryl contains one, two or three heteroatoms selected from N, O andS; wherein Q^(2a) is selected from halogen, C₁-C₆-alkoxy,C₃-C₆-halogencycloalkyl, phenyl that is unsubstituted or substituted by1, 2, 3, 4 or 5 substituents Q^(22a) independently selected fromC₁-C₄-alkyl; and wherein the aliphatic moieties of Q² are unsubstitutedor substituted with identical or different groups Q^(2a) as definedbelow and wherein the cycloalkyl moieties of Q² are not furthersubstituted or carry one, two, three, four or five identical ordifferent groups Q^(2b) as defined below.

According to a further embodiment, Q² is independently selected fromhydrogen, halogen C₁-C₆-alkyl, C₁-C₆-halogenalkyl, in particularindependently selected from hydrogen, C₁-C₄-alkyl andC₁-C₄-halogenalkyl.

Q^(2a) are the possible substituents for the aliphatic moieties of Q².

Q^(2a) according to the invention is independently selected fromhalogen, C₁-C₆-alkoxy, C₃-C₆-halogencycloalkyl, and phenyl, wherein thephenyl group is unsubstituted or carries one, two, three, four or fivesubstituents R^(42a) selected from the group consisting of halogen, OH,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy,in particular selected from halogen, C₁-C₂-alkyl, C₁-C₂-halogenalkyl,C₁-C₂-alkoxy and C₁-C₂-halogenalkoxy, more specifically selected fromhalogen, such as F, Cl and Br.

According to one embodiment Q^(2a) is independently selected fromhalogen, OH, CN, C₁-C₂-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyland C₁-C₂-halogenalkoxy. Specifically, Q^(2a) is independently selectedfrom F, C, OH, CN, C₁-C₂-alkoxy, cyclopropyl, 1-F-cyclopropyl,1-Cl-cyclopropyl and C₁-C₂-halogenalkoxy.

According to one particular embodiment Q^(2a) is independently selectedfrom halogen, such as F, C, Br and I, more specifically F, Cl and Br.

According to a further embodiment, Q^(2a) is independently selected fromOH, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.Specifically, Q^(2a) is independently selected from OH, cyclopropyl andC₁-C₂-halogenalkoxy.

Q^(2b) are the possible substituents for the cycloalkyl, heteroaryl andaryl moieties of Q².

Q^(2b) according to the invention is independently selected fromhalogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₄-halogenalkoxy.

According to one embodiment thereof Q^(2b) is independently selectedfrom halogen, CN, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.Specifically, Q^(2b) is independently selected from F, C, OH, CN, CH₃,OCH₃, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl and halogenmethoxy.

According to a further embodiment thereof Q^(2b) is independentlyselected from C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and C₁-C₂-halogenalkoxy.

Specifically, Q^(2b) is independently selected from OH, CH₃, OCH₃cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl and halogenmethoxy, morespecifically independently selected from OH, CH₃, OCH₃ cyclopropyl,1-F-cyclopropyl, 1-Cl-cyclopropyl and OCHF₂.

Particularly preferred embodiments of Q² according to the invention arein Table Q1 below, wherein each line of lines Q2-1 to Q2-39 correspondsto one particular embodiment of the invention, wherein Q2-1 to Q2-39 arealso in any combination with one another a preferred embodiment of thepresent invention:

TABLE Q2 No. Q1 Q2-1 H Q2-2 F Q2-3 Cl Q2-4 CH₃ Q2-5 CH₂CH₃ Q2-6 iPr Q2-7cPr Q2-8 CF₃ Q2-9 CHF₂ Q2-10 CH₂F Q2-11 CCl₃ Q2-12 CHCl₂ Q2-13 CH₂ClQ2-14 CH₂CF₃ Q2-15 CH₂CCl₃ Q2-16 CHF₂CF₂ Q2-17 OCH₃ Q2-18 OCH₂CH₃ Q2-19OCF₃ Q2-20 OCHF₂ Q2-21 OCH₂F Q2-22 OCF₂CHF₂ Q2-23 OCCl₃ Q2-24 OCHCl₂Q2-25 OCH₂Cl Q2-26 CCH Q2-27 OC≡CH Q2-28 CH═CH₂ Q2-29 CH₂CH═CH₂ Q2-30OCH═CH₂ Q2-31 OCH₂CH═CH₂ Q2-32 Ph Q2-33 CH₂Ph Q2-34 3-py Q2-35 2-pyQ2-36 4-py Q2-37

Q2-38

Q2-39

Q¹ and Q² according to the present invention form, together with thecarbon atom to which they are bound form a three- to seven-memberedsaturated or partially unsaturated carbo- or heterocycle, wherein thering may further contain 1, 2, 3 or 4 heteroatoms selected from N—R^(N),O and S, wherein R^(N) is selected from H, C₁-C₄-alkyl and SO₂R^(Q);wherein

-   R^(Q) is selected from C₁-C₄-alkyl, C₁-C₄-halogenalkyl,    unsubstituted aryl or heteroaryl that is substituted by 1, 2, 3, 4    or 5 substituents R¹ independently selected from C₁-C₄-alkyl; and    wherein S may be in the form of its oxide SO or SO₂; and wherein in    each case one or two CH₂ groups of the carbo- or heterocycle may be    replaced by a group independently selected from C(═O) and C(═S);    and wherein the ring is unsubstituted or substituted with 1, 2, 3,    4, 5 or up to the maximum number of identical or different groups    R^(QR) which independently of one another are selected from:    Q^(R) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,    C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

According to one embodiment, the carbocycle formed by Q¹ and Q² issaturated.

According to a further embodiment, the carbocycle formed by Q¹ and Q² isa saturated unsubstituted or substituted carbocycle. According to oneembodiment, this saturated carbocycle is unsubstituted. According to afurther embodiment, the saturated carbocycle carries one, two, three orfour substituents Q^(QR). In one further particular embodiment, saidcarbocycle is cyclopropane. In one further particular embodiment, saidcarbocycle is cyclobutane. In one further particular embodiment, saidcarbocycle is cyclohexane. In one further particular embodiment, saidcarbocycle is cyclopentane. In one further particular embodiment, saidcarbocycle is cyclopropane substituted by halogene or C₁-C₄-alkyl. Inone further particular embodiment, said carbocycle is cyclobutanesubstituted by halogene or C₁-C₄-alkyl. In one further particularembodiment, said carbocycle is cyclohexane substituted by halogene orC₁-C₄-alkyl. In one further particular embodiment, said carbocycle iscyclopentane substituted by halogene or C₁-C₄-alkyl.

According to a further embodiment, the unsubstituted or substituted andsaturated or partially unsaturated heterocycle is three-, four-, five-or six-membered and contains one, two or three, more particularly one ortwo, heteroatoms selected from NH, NR^(N), O, S, S(═O) and S(═O)₂,wherein R^(N) is as defined above or preferably selected fromC₁-C₂-alkyl, C₁-C₂-halogenalkyl and SO₂Ph, wherein Ph is unsubstitutedphenyl or phenyl that is substituted by one C₁-C₂-alkyl. In one furtherparticular embodiment, said heterocycle is four- or six-membered.

According to a further embodiment, the heterocycle formed by Q¹ and Q²contains one, two or three, more specifically one or two, heteroatomsselected from NH and NR^(N), wherein R^(N) is as defined and preferablydefined below, more particularly selected from C₁-C₂-alkyl,C₁-C₂-halogenalkyl and SO₂Ph, wherein Ph is unsubstituted phenyl orphenyl that is substituted by one methyl.

In one embodiment thereof, it contains one or two heteroatoms NH, inparticular one NH. In another embodiment, it contains one or twoheteroatoms NR^(N), in particular one NR^(N), wherein R^(N) in each caseis as defined and preferably defined above.

According to a further embodiment, the heterocycle formed by Q¹ and Q²contains one, two or three, more specifically one or two, in particularone, heteroatom(s) selected from S, S(═O) and S(═O)₂. In one embodimentthereof, it contains one or two heteroatoms S, in particular one S. Inanother embodiment, it contains one or two heteroatoms S(═O), inparticular one S(═O). In still another embodiment, it contains one ortwo heteroatoms S(═O)₂, in particular one S(═O)₂.

According to a further embodiment, the heterocycle formed by Q¹ and Q²contains one or two heteroatoms 0. In one embodiment thereof, itcontains one heteroatom 0. In another embodiment, it contains twoheteroatoms 0.

According to a further embodiment, the heterocycle formed by Q¹ and Q²is unsubstituted, i.e. it does not carry any substituent Q^(QR).According to a further embodiment, it carries one, two, three or fourQ^(R).

According to one particular embodiment, Q¹ and Q² together form a4-membered saturated heterocycle which contains 1 or 2 heteroatoms, inparticular 1 heteroatom, from the group consisting of NH, NR^(N), O, S,S(═O) and S(═O)₂, as ring members, wherein R^(N) is defined andpreferably defined above. In one embodiment, the heterocycle containsone O as heteroatom. For example, the formed heterocycle is oxetane.According to one embodiment thereof, the heterocycle is unsubstituted,i.e. it does not carry any substituent Q^(QR). According to a furtherembodiment, it carries one, two, three or four Q^(R).

According to a further particular embodiment, Q¹ and Q² together form a5-membered saturated heterocycle which contains 1, 2 or 3, in particular1 or 2, heteroatoms from the group consisting of NH, NR^(N), O, S, S(═O)and S(═O)₂, as ring members, wherein R^(N) is as defined and preferablydefined above. According to one embodiment thereof, the heterocycle isunsubstituted, i.e. it does not carry any substituent Q^(QR). Accordingto a further embodiment, it carries one, two, three or four Q^(R).

According to a further particular embodiment, Q¹ and Q² together form a6-membered saturated heterocycle which contains 1, 2 or 3, in particular1 or 2, heteroatoms from the group consisting of NH, NR^(N), O, S, S(═O)and S(═O)₂, as ring members, wherein R^(N) is as defined and preferablydefined below. According to one embodiment thereof, the heterocycle isunsubstituted, i.e. it does not carry any substituent Q^(QR). Accordingto a further embodiment, it carries one, two, three or four Q^(R).According to one specific embodiment thereof, said 6-membered saturatedheterocycle contains 1 or 2 heteroatoms selected from NH and NR^(N).According to a further specific embodiment thereof, said 6-memberedsaturated heterocycle contains 1 or 2 heteroatoms 0.

According to a further specific embodiment thereof, said 6-memberedsaturated heterocycle contains 1 or 2 heteroatoms selected from S, S(═O)and S(═O)₂. According to one embodiment thereof, the respective6-membered heterocycle is unsubstituted, i.e. it does not carry anysubstituent Q^(QR). According to a further embodiment, it carries one,two, three or four Q^(R).

According to a further particular embodiment, Q¹ and Q² together form athree- to six-membered saturated or partially unsaturated carbo-, orheterocycle.

Q^(QR) are the possible substituents for the heterocycle formed by Q¹and Q² and are independently selected from halogen, OH, CN, NO₂, SH,NH₂, C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio, C₁-C₄-alkoxy-C₁-C₄-alkyl,phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carryone, two, three, four or five substituents Q^(R) selected from the groupconsisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxyand C₁-C₄-halogenalkoxy; and wherein in each case one or two CH₂ groupsof the carbo- or heterocycle may be replaced by a group independentlyselected from C(═O) and C(═S).

In one preferred embodiment, Q^(QR) is in each case independentlyselected from halogen, OH, CN, SH, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy and C₁-C₆-alkylthio. In one furtherpreferred embodiment, Q^(QR) is in each case independently selected fromhalogen, C₁-C₆-alkyl and C₁-C₆-halogenalkyl. In one further particularembodiment, Q^(QR) is in each case independently selected fromC₁-C₆-alkyl, such as methyl and ethyl.

R^(N) is the substituent of the heteroatom NR^(N) that is contained inthe heterocycle formed by Q² and Q³ in some of the inventive compounds.R^(N) is selected from C₁-C₄-alkyl, C₁-C₄-halogenalk and SO₂Ph, whereinPh is unsubstituted phenyl or phenyl that is substituted by one, two orthree substituents selected from C₁-C₄-alkyl. In one preferredembodiment, R^(N) is in each case independently selected fromC₁-C₂-alkyl, C₁-C₂-halogenalkyl and SO₂Ph, wherein Ph is unsubstitutedphenyl or phenyl that is substituted by one methyl substituents. In oneparticular embodiment, R^(N) is in each case independently selected fromC₁-C₂-alkyl, more particularly methyl. In one particular embodiment,R^(N) is in each case independently selected from SO₂Ph, wherein Ph isunsubstituted phenyl or phenyl that is substituted by one methyl.

Particularly preferred embodiments of the heterocycles formed Q¹ and Q²and according to the invention are in Table Q12 below, wherein each lineof lines Q12-1 to Q12-15 corresponds to one particular embodiment of theinvention, wherein Q12-1 to Q12-15 are also in any combination with oneanother a preferred embodiment of the present invention. The carbonatom, to which Q¹ and Q² are bound is marked with # in the drawings.

TABLE Q12 No. heterocycle formed by Q¹ and Q² Q12-1

Q12-2

Q12-3

Q12-4

Q12-5

Q12-6

Q12-7

Q12-8

Q12-9

Q12-10

Q12-11

Q12-12

Q12-13

Q12-14

Q12-15

W according to the invention is O, S(O)_(m) or NQ⁴; wherein m is 0, 1 or2.

According to one embodiment of formula I, W is O.

According to another embodiment of formula I, W is S.

According to another embodiment of formula I, W is SO.

According to another embodiment of formula I, W is SO₂.

According to another embodiment of formula I, U is CR³ and W is NQ⁴

According to one most preferred embodiment of formula I, U is N and W isO.

According to one further most preferred embodiment of formula I, U is Nand W is S

According to one further most preferred embodiment of formula I, U is Nand W is SO.

According to one further most preferred embodiment of formula I, U is Nand W is SO₂.

According to one further most preferred embodiment of formula I, U is Nand W is NQ⁴.

Q³ according to the invention is selected from substituted C₁-C₁₅-alkyl,C₂-C₁₅-alkenyl, C₂-C₁₅-halogenalkenyl, C₂-C₁₅-alkynyl, C₃-C₇-cycloalkyl,S(O)_(m)—C₁-C₁₅-alkyl, S(O)_(m)—C₁-C₁₅-alkoxy, S(O)_(m)-aryl,S(O)_(m)—C₂-C₁₅-alkenyl, S(O)_(m)—C₂-C₁₅-alkynyl, C(═O)C₁-C₁₅-alkyl,C(═O)C₁-C₁₅-halogenalkyl, C(═O)C₂-C₁₅-alkenyl, C(═O)C₂-C₁₅-alkynyl,C(═O)C₃-C₇-cycloalkyl, C(═O)aryl, C(═O)NH(C₁-C₁₅-alkyl),C(═O)N(C₁-C₁₅-alkyl)₂, C(═O)NH(C₂-C₁₅-alkenyl), C(═O)N(C₂-C₁₅-alkenyl),C(═O)NH(C₂-C₁₅-alkynyl), C(═O)N(C₂-C₁₅-alkynyl),C(═O)NH(C₃-C₇-cycloalkyl), C(═O)N(C₃-C₇-cycloalkyl), C(═S)C₁-C₁₅-alkyl,C(═S)C₂-C₁₅-alkenyl, C(═S)C₂-C₁₅-alkynyl, C(═S)C₃-C₆-cycloalkyl,C(═S)O(C₁-C₁₅-alkyl), C(═S)O(C₂-C₁₅-alkenyl), C(═S)O(C₂-C₁₅-alkynyl),C(═S)O(C₃-C₇-cycloalkyl), C(═S)NH(C₁-C₁₅-alkyl),C(═S)NH(C₂-C₁₅-alkenyl), C(═S)NH(C₂-C₁₅-alkynyl),C(═S)NH(C₃-C₇-cycloalkyl), C(═S)N(C₁-C₁₅-alkyl)₂,C(═S)N(C₂-C₁₅-alkenyl), C(═S)N(C₂-C₁₅-alkynyl)₂,C(═S)N(C₃-C₇-cycloalkyl), C₃-C₆-cycloalkyl, three-, four-, five- orsix-membered saturated or partially unsaturated heterocycle, five- orsix-membered heteroaryl and aryl; wherein the heteroaryl contains one,two or three heteroatoms selected from N, O and S; wherein in each caseone or two CH₂ groups of the carbocycle and heterocycle may be replacedby a group independently selected from C(═O) and C(═S)

wherein the aliphatic moieties of Q³ except for substituted C₁-C₁₅-alkylmoieties are unsubstituted or substituted with identical or differentgroups Q^(3a) which independently of one another are selected from:

-   Q^(3a) halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),    N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,    NH—SO₂—R^(x), C₁-C₆-halogenalkylthio, S(O)_(m)—C₁-C₆-alkyl,    S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl, CH(═O),    C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),    C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    phenyl, phenoxy and five- to ten-membered heterocycle, heteroaryl,    heterocycloxy, heteryloxy; wherein in each case one or two CH₂    groups of the carbocycle and heterocycle may be replaced by a group    independently selected from C(═O) and C(═S); wherein the heterocycle    or heteroaryl contains one, two or three heteroatoms selected from    N, O and S; wherein the phenyl, phenoxy, heterocycle and heteroaryl    groups are unsubstituted or substituted with 1, 2, 3, 4 or 5    substituents Q^(31a) selected from the group consisting of halogen,    OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,    NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x),    C₁-C₆-alkylthio, S(O)_(m)—C₁-C₆-alkyl, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, CR′═NOR″;    phenyl, phenoxy and five- to ten-membered heterocycle and    heteroaryl; wherein the heterocycle or heteroaryl contains one, two    or three heteroatoms selected from N, O and S; and wherein the    phenyl, phenoxy, heterocycle and heteroaryl groups are unsubstituted    or substituted with 1, 2, 3, 4 or 5 substituents Q^(311a) selected    from the group consisting of halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, CN, CR′═NOR″ and    C₁-C₄-halogenalkoxy; and wherein m, R^(x), R′ and R″ is defined as    above;    wherein the carbocycle, heterocycle, heteroaryl and aryl moieties of    Q³ are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the    maximum number of identical or different groups Q³ which    independently of one another are selected from:-   Q^(3b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,    C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio,    phenyl, phenoxy and five- to ten-membered heterocycle, heteroaryl,    heterocycloxy, heteryloxy; wherein the heterocycle or heteroaryl    contains one, two or three heteroatoms selected from N, O and S;    wherein the phenyl, phenoxy, heterocycle and heteroaryl groups are    unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents    Q^(31b) selected from the group consisting of halogen, OH,    C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,    CR′═NOR″; phenyl, phenoxy and five- to ten-membered heterocycle and    heteroaryl; wherein the heterocycle or heteroaryl contains one, two    or three heteroatoms selected from N, O and S; and wherein the    phenyl, phenoxy, heterocycle and heteroaryl groups are unsubstituted    or substituted with 1, 2, 3, 4 or 5 substituents Q^(31l) selected    from the group consisting of halogen, OH, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, CN, CR′═NOR″ and    C₁-C₄-halogenalkoxy; and wherein R′ and R″ are defined as above.    wherein the substituted C₁-C₁₅-alkyl moieties of Q³ carry one, two,    three or up to the maximum possible number of identical or different    groups Q^(3c), respectively, which independently of one another are    selected from:-   Q^(3c) halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),    N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,    NH—SO₂—R^(x), C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,    C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio,    S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m),-aryl,    CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),    C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, a saturated or partially unsaturated    three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered    carbocycle or heterocycle, aryl and five-, six- or ten-membered    heteroaryl, heterocycloxy, heteryloxy; wherein in each case one or    two CH₂ groups of the carbocycle and heterocycle may be replaced by    a group independently selected from C(═O) and C(═S); wherein the    heterocycle and heteroaryl contain independently one, two, three or    four heteroatoms selected from N, O and S; wherein the carbocyclic,    heterocyclic, aryl, phenoxy and heteroaryl groups are independently    unsubstituted or carry one, two, three, four or five substituents    Q^(31c) selected from the group consisting of s halogen, OH, CN,    NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,    NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x),    C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy,    C₁-C₄-halogenalkoxy, S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″; phenyl,    phenoxy and five- to ten-membered heterocycle and heteroaryl;    wherein the heterocycle or heteroaryl contains one, two or three    heteroatoms selected from N, O and S; and wherein the carbocyclic,    heterocyclic, phenyl, phenoxy, heterocycle and heteroaryl groups are    unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents    Q^(31c) selected from the group consisting of halogen, OH, CN, NO₂,    SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),    N(C(═O)C₁-C₄-alkyl), NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl,    C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy and    S(O)_(m)—C₁-C₆-alkyl; wherein m, R^(x), R′ and R″ is as defined    above;

According to still another embodiment of formula I, Q³ isC₁-C₁₅-halogenalkyl, in particular C₁-C₇-halogenalkyl, such as CF₃,CCl₃, FCH₂, ClCH₂, F₂CH, Cl₂CH, CF₃CH₂, CCl₃CH₂ or CF₂CHF₂.

According to still a further embodiment of formula I, Q³ isC₂-C₁₅-alkenyl, in particular C₂-C₇-alkenyl, such as CH═CH₂, C(CH₃)═CH₂,CH₂CH═CH₂.

According to a further specific embodiment of formula I, Q³ isC₂-C₁₅-alkenyl, in particular C₂-C₇-alkenyl, more specificallyC₂-C₄-alkenyl such as CH═CH₂, CH₂CH═CH₂ or CH₂, CH₂CH═CH₂

According to a further specific embodiment of formula I, Q³ isC₂-C₁₅-halogenalkenyl, in particular C₂-C₇-halogenalkenyl, morespecifically C₂-C₃-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF₂,CH═CCl₂, CH₂CH═CHF, CH₂CH═CHCl, CH₂CH═CF₂, CH₂CH═CCl₂, CF₂CH═CF₂,CCl₂CH═CCl₂, CF₂CF═CF₂, CCl₂CCl═CCl₂.

According to still a further embodiment of formula I, Q³ isC₂-C₁₅-alkynyl or C₂-C₁₅-halogenalkynyl, in particular C₂-C₄-alkynyl orC₂-C₄-halogenalkynyl, such as C≡CH, CH₂C≡CH.

According to still another embodiment of formula I Q³ isC₃-C₇-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I, Q³ isC₃-C₇-halogencycloalkyl. In a special embodiment R^(3b) is fully orpartially halogenated cyclopropyl, such as 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl.

According to still another embodiment of formula I, Q³ isS(O)_(m)—C₁-C₁₅-alkyl such as SCH₃, S(═O) CH₃, S(O)₂CH₃.

According to still another embodiment of formula I, Q³ isS(O)_(m)—C₁-C₁₅-halogenalkyl such as SCF₃, S(═O)CF₃, S(O)₂CF₃, SCHF₂,S(═O)CHF₂, S(O)₂CHF₂.

According to still another embodiment of formula I, Q³ isS(O)_(m)—C₁-C₁₅-alkoxy such as S(OCH₃), S(═O)(OCH₃), S(O)₂(OCH₃).

According to still another embodiment of formula I, Q³ is S(O)_(m)-arylsuch as S-phenyl, S(═O) phenyl, S(O)₂phenyl, wherein the phenyl group isunsubstituted or carries one, two, three, four or five substituentsR^(78a) selected from the group consisting of halogen, OH, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;

According to still another embodiment of formula I, Q³ isS(O)n-C₂-C₆-alkenyl such as SCH═CH₂, S(═O)CH═CH₂, S(O)₂CH═CH₂,SCH₂CH═CH₂, S(═O)CH₂CH═CH₂, S(O)₂CH₂CH═CH₂.

According to still another embodiment of formula I, Q³ isS(O)n-C₂-C₆-alkynyl such as SC≡CH, S(═O)C≡CH, S(O)₂C≡CH, SCH₂C≡CH,S(═O)CH₂C≡CH, S(O)₂CH₂C≡CH.

According to a further specific embodiment of formula I, Q³ isC(═O)C₁-C₁₅-alkyl, wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, Q³ isC(═O)C₁-C₁₅-halogenalkyl, wherein halogenalkyl is CF₃, CCl₃, FCH₂,ClCH₂, F₂CH, C₂CH, CF₃CH₂, CCl₃CH₂ or CF₂CHF₂.

According to a further specific embodiment of formula I, Q³ isC(═O)C₂-C₁₅-alkenyl, wherein alkenyl is CH═CH₂, CH₂CH═CH₂.

According to a further specific embodiment of formula I, Q³ isC(═O)C₂-C₁₅-alkynyl, wherein alkynyl is C≡CH, CH₂C≡CH.

According to a further specific embodiment of formula I, Q³ isC(═O)C₃-C₇-cycloalkyl, wherein cycloalkyl is cyclopropyl (C₃H₇) orcyclobutyl (C₄H₉).

According to a further specific embodiment of formula I, Q³ isC(═O)aryl, wherein the phenyl group is unsubstituted or carries one,two, three, four or five substituents R^(78a) selected from the groupconsisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxyand C₁-C₄-halogenalkoxy.

According to a further specific embodiment of formula I, Q³ isC(═O)NH(C₁-C₁₅-alkyl) or C(═O)N(C₁-C₁₅-alkyl)₂, wherein alkyl is CH₃,C₂H₅, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl ori-pentyl.

According to a further specific embodiment of formula I, Q³ isC(═O)NH(C₂-C₁₅-alkenyl) or C(═O)N(C₂-C₁₅-alkenyl)₂), wherein alkenyl isCH═CH₂, CH₂CH═CH₂.

According to a further specific embodiment of formula I, Q³ isC(═O)NH(C₂-C₁₅-alkynyl) or C(═O)N(C₂-C₁₅-alkynyl)₂, wherein alkynyl isC≡CH, CH₂C≡CH.

According to a further specific embodiment of formula I, Q³ isC(═O)NH(C₃-C₇-cycloalkyl) or C(═O)N(C₃-C₇-cycloalkyl)₂, whereincycloalkyl is cyclopropyl (C₃H₇) or cyclobutyl (C₄H₉).

According to a further specific embodiment of formula I, Q³ isC(═S)C₁-C₁₅-alkyl, C(═S)O(C₁-C₁₅-alkyl), C(═S)NH(C₁-C₅-alkyl) orC(═S)N(C₁-C₁₅-alkyl)₂, wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, Q³ isC(═S)C₂-C₁₅-alkenyl, C(═S)O(C₂-C₁₅-alkenyl), C(═S)NH(C₂-C₁₅-alkenyl) orC(═S)N(C₂-C₁₅-alkenyl)₂, wherein alkenyl is CH═CH₂, CH₂CH═CH₂.

According to a further specific embodiment of formula I, Q³ isC(═S)O(C₂-C₁₅-alkynyl), C(═S)NH(C₂-C₁₅-alkynyl) orC(═S)N(C₂-C₁₅-alkynyl), wherein alkynyl is C≡CH, CH₂C≡CH.

According to a further specific embodiment of formula I, Q³ isC(═S)C₃-C₇-cycloalkyl, C(═S)O(C₃-C₇-cycloalkyl) orC(═S)N(C₃-C₇-cycloalkyl)₂, wherein cycloalkyl is cyclopropyl (C₃H₇) orcyclobutyl (C₄H₉).

According to still another embodiment of formula I, Q³ is a partiallyunsaturated three-, four-, five-, six-, seven-, eight-, nine-, orten-membered carbocycle, in particular three-, four-, five- orsix-membered, wherein the carbocycle is unsubstituted or substituted bysubstituents Q^(3b) as defined below. According to one embodimentthereof, the carbocycle is unsubstituted.

According to still another embodiment of formula I, Q³ is a partiallyunsaturated three-, four-, five-, six-, seven-, eight-, nine-, orten-membered carbocycle or heterocycle, in particular three-, four-,five- or six-membered, wherein the heterocycle contains one, two, threeor four heteroatoms selected from N, O and S, and wherein the carbocycleand heterocycle are unsubstituted or substituted with substituentsQ^(3b) as defined below. According to one embodiment thereof, thecarbocycle or heterocycle is unsubstituted.

According to still a further embodiment, Q³ is a saturated three-,four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle orheterocycle, in particular three-, four-, five- or six-membered, whereinthe heterocycle contains one, two, three or four heteroatoms selectedfrom N, O and S, and wherein the carbocycle and heterocycle areunsubstituted or substituted with substituents Q^(3b) as defined below.According to one embodiment thereof, the carbocycle or heterocycle isunsubstituted.

According to still another embodiment of formula I, Q³ is a saturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedcarbocycle, in particular three-, four-, five- or six-membered, whereinthe carbocycle is unsubstituted or substituted by substituents Q^(3b) asdefined below. According to one embodiment thereof, the carbocycle isunsubstituted.

According to one embodiment, Q³ is a 3-membered saturated carbocycle.According to one embodiment thereof, the carbocycle is unsubstituted,i.e. it does not carry any substituent Q³

According to still another embodiment of formula I, it is substituted byQ³

According to one embodiment, Q³ is a 3-membered saturated carbocycle,which is unsubstituted such as cyclopropyl.

According to one embodiment, Q³ is a 3-membered saturated carbocycle,which is substituted by halogen, more specifically by F, such as C₃H₃F₂.

According to one embodiment, Q³ is a 3-membered saturated carbocycle,which is substituted by halogen. More specifically by C, such asC₃H₃Cl₂.

According to one embodiment, Q³ is a 4-membered saturated carbocycle.According to one embodiment thereof, the carbocycle is unsubstituted,i.e. it does not carry any substituent Q^(3b).

According to still another embodiment of formula I, it is substituted byQ^(3b)

According to one embodiment, Q³ is a 5-membered saturated carbocycle.According to one embodiment thereof, the carbocycle is unsubstituted,i.e. it does not carry any substituent Q^(3b)

According to still another embodiment of formula I, it is substituted byQ^(3b)

According to one embodiment, Q³ is a 6-membered saturated carbocycle.According to one embodiment thereof, the carbocycle is unsubstituted,i.e. it does not carry any substituent Q^(3b)

According to still another embodiment of formula I, it is substituted byQ^(3b)

According to still another embodiment of formula I, Q³ is a partiallyunsaturated three-, four-, five-, six-, seven-, eight-, nine-, orten-membered heterocycle, in particular three-, four-, five- orsix-membered, wherein the heterocycle contains one, two, three or fourheteroatoms selected from N, O and S, and wherein the heterocycle isunsubstituted or substituted by substituents R^(4b) as defined below.According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, Q³ is a saturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedheterocycle, in particular three-, four-, five- or six-membered, whereinthe heterocycle contains one, two, three or four heteroatoms selectedfrom N, O and S, and wherein the heterocycle is unsubstituted orsubstituted by substituents R⁴ as defined below. According to oneembodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, in the embodimentsof Q³ described above, the heterocycle contains preferably one, two orthree, more specifically one or two heteroatoms selected from N, O andS. More specifically, the hetereocycle contains one heteroatom selectedfrom N, O and S. In particular, the heterocycle contains one or two, inparticular one O.

According to one embodiment, Q³ is a 4-membered saturated heterocyclewhich contains 1 or 2 heteroatoms, in particular 1 heteroatom, from thegroup consisting of N, O and S, as ring members.

According to one embodiment, the heterocycle contains one O asheteroatom. For example, the formed heterocycle is oxetane. According toone embodiment thereof, the heterocycle is unsubstituted, i.e. it doesnot carry any substituent Q³. According to still another embodiment offormula I, it is substituted by Q³

According to still another embodiment of formula I, Q³ is a 5-memberedsaturated heterocycle which contains 1, 2 or 3, in particular 1 or 2,heteroatoms from the group consisting of N, O and S, as ring members.According to one embodiment, the heterocycle contains one O asheteroatom.

According to one embodiment thereof, the heterocycle is unsubstituted,i.e. it does not carry any substituent Q³. According to still anotherembodiment of formula I, it is substituted by Q^(3b).

According to still another embodiment of formula I, Q³ is a 6-memberedsaturated heterocycle which contains 1, 2 or 3, in particular 1 or 2,heteroatoms from the group consisting of N, O and S as ring members.According to one embodiment thereof, the heterocycle is unsubstituted,i.e. it does not carry any substituent Q^(3b). According to stillanother embodiment of formula I, it is substituted by Q^(3b). Accordingto one specific embodiment thereof, said 6-membered saturatedheterocycle contains 1 or 2, in particular 1, heteroatom(s) O. Accordingto one embodiment thereof, the respective 6-membered heterocycle isunsubstituted, i.e. it does not carry any substituent Q^(3b) Accordingto still another embodiment of formula I, it is substituted by Q^(3b)

According to still another embodiment of formula I, Q³ is aryl, inparticular phenyl, wherein the aryl or phenyl moiety in each case isunsubstituted or substituted by identical or different groups R^(3b)which independently of one another are selected from halogen,C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl and C₁-C₂-halogenalkoxy,in particular F, Cl, Br, CH₃, OCH₃, CF₃ and OCF₃. According to oneembodiment, Q³ is unsubstituted phenyl. According to another embodiment,Q³ is phenyl, that is substituted by one, two or three, in particularone, halogen, in particular selected from F, Cl and Br, morespecifically selected from F and Cl.

According to still another embodiment of formula I, Q³ is a 5-memberedheteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl,thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl,pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl,imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl,isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl,1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.

According to still another embodiment of formula I, Q³ is a 6-memberedheteroaryl such as pyri-din-2-yl, pyridin-3-yl, pyridin-4-yl,pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and1,2,4-triazin-3-yl.

According to still another embodiment of formula I, Q³ is in each caseindependently selected from substituted C₁-C₁₅-alkyl, C₂-C₁₅-alkenyl,C₂-C₁₅-halogenalkenyl, C₂-C₁₅-alkynyl, C₃-C₇-cycloalkyl,C(═O)C₁-C₁₅-alkyl, C(═O)C₁-C₁₅-halogenalkyl, C(═O)aryl, three-, four-,five- or six-membered saturated or partially unsaturated heterocycle,five- or six-membered heteroaryl, and aryl; wherein the heterocycle andheteroaryl contains one, two or three heteroatoms selected from N, O andS; wherein in each case one or two CH₂ groups of the carbocycle andheterocycle may be replaced by a group independently selected from C(═O)and C(═S); wherein the acyclic moieties of Q³ except for substitutedC₁-C₁₅-alkyl moieties are unsubstituted or substituted with identical ordifferent groups Q^(3a) as defined and preferably defined herein;wherein the carbocyclic, phenyl and heteroaryl moieties of Q³ areunsubstituted or substituted with identical or different groups Q³ asdefined and preferably defined herein; and wherein the substitutedC₁-C₁₅-alkyl moieties of Q³ are or substituted with identical ordifferent groups Q^(3c) as defined and preferably defined herein.

According to still another embodiment of formula I, Q³ is in each caseindependently selected from substituted C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, and C₃-C₆-cycloalkyl, wherein in each case one or two CH₂groups of the carbocycle and heterocycle may be replaced by a groupin-dependently selected from C(═O) and C(═S); wherein the acyclicmoieties of Q³ except for substituted C₁-C₁₅-alkyl moieties areunsubstituted or substituted with identical or different groups Q^(3a)as defined and preferably defined herein; wherein the carbocyclic,phenyl and heteroaryl moieties of Q³ are unsubstituted or substitutedwith identical or different groups Q^(3b) as defined and preferablydefined herein; and wherein the substituted C₁-C₁₅-alkyl moieties of Q³are or substituted with identical or different groups Q^(3c) as definedand preferably defined herein.

According to still another embodiment of formula I, Q³ is in each caseindependently selected from C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl) andC(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl), C(═O)C₂-C₆-alkenyl,C(═O)O(C₂-C₆-alkenyl), C(═O)NH(C₂-C₆-alkenyl), C(═O)N(C₂-C₆-alkenyl),C(═O)C₂-C₆-alkynyl, C(═O)O(C₂-C₆-alkynyl), C(═O)NH(C₂-C₆-alkynyl),C(═O)N(C₂-C₆-alkynyl)₂C(═O)C₃-C₆-cycloalkyl, C(═O)O(C₃-C₆-cycloalkyl),C(═O)NH(C₃-C₆-cycloalkyl) and C(═O)N(C₃-C₆-cycloalkyl)₂, wherein in eachcase one or two CH₂ groups of the carbocycle and heterocycle may bereplaced by a group independently selected from C(═O) and C(═S); whereinthe acyclic moieties of Q³ except for substituted C₁-C₁₅-alkyl moietiesare unsubstituted or substituted with identical or different groupsQ^(3a) as defined and preferably defined herein; wherein thecarbocyclic, phenyl and heteroaryl moieties of Q³ are unsubstituted orsubstituted with identical or different groups Q^(3b) as defined andpreferably defined herein; and wherein the substituted C₁-C₁₅-alkylmoieties of Q³ are or substituted with identical or different groupsQ^(3c) as defined and preferably defined herein.

According to still another embodiment of formula I, Q³ is in each caseindependently selected from C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl),C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂, C(═O)C₂-C₆-alkenyl,C(═O)O(C₂-C₆-alkenyl), C(═O)NH(C₂-C₆-alkenyl), C(═O)N(C₂-C₆-alkenyl)₂;wherein in each case one or two CH₂ groups of the carbocycle andheterocycle may be replaced by a group independently selected from C(═O)and C(═S); wherein the acyclic moieties of Q³ except for substitutedC₁-C₁₅-alkyl moieties are unsubstituted or substituted with identical ordifferent groups Q^(3a) as defined and preferably defined herein;wherein the carbocyclic, phenyl and heteroaryl moieties of Q³ areunsubstituted or substituted with identical or different groups Q^(3b)as defined and preferably defined herein; and wherein the substitutedC₁-C₁₅-alkyl moieties of Q³ are or substituted with identical ordifferent groups Q^(3c) as defined and preferably defined herein.

According to still another embodiment of formula I, Q³ is in each caseindependently selected from SO₂—NH(C₁-C₆-alkyl),SO₂—NH(C₁-C₆-halogenalkyl), SO₂—NHphenyl; wherein in each case one ortwo CH₂ groups of the carbocycle and heterocycle may be replaced by agroup independently selected from C(═O) and C(═S); wherein the acyclicmoieties of Q³ except for substituted C₁-C₁₅-alkyl moieties areunsubstituted or substituted with identical or different groups Q^(3a)as defined and preferably defined herein; wherein the carbocyclic,phenyl and heteroaryl moieties of Q³ are unsubstituted or substitutedwith identical or different groups Q^(3b) as defined and preferablydefined herein; and wherein the substituted C₁-C₁₅-alkyl moieties of Q³are or substituted with identical or different groups Q^(3c) as definedand preferably defined herein.

According to still another embodiment of formula I, Q³ is in each caseindependently selected from substituted C₁-C₆-alkyl, C(═O)C₁-C₆-alkyl,C(═O)O(C₁-C₆-alkyl), S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)aryl; wherein in eachcase one or two CH₂ groups of the carbocycle and heterocycle may bereplaced by a group independently selected from C(═O) and C(═S); whereinthe acyclic moieties of Q³ except for substituted C₁-C₁₅-alkyl moietiesare unsubstituted or substituted with identical or different groupsQ^(3a) as defined and preferably defined herein; wherein thecarbocyclic, phenyl and heteroaryl moieties of Q³ are unsubstituted orsubstituted with identical or different groups Q^(3b) as defined andpreferably defined herein; and wherein the substituted C₁-C₁₅-alkylmoieties of Q³ are or substituted with identical or different groupsQ^(3c) as defined and preferably defined herein.

According to still another embodiment of formula I, Q³ is in each caseindependently selected from substituted C₁-C₁₅-alkyl, C₂-C₁₅-alkenyl,C₂-C₁₅-halogenalkenyl, C₂-C₁₅-alkynyl, C(═O)C₁-C₁₅-alkyl,C(═O)C₁-C₁₅-halogenalkyl, wherein the acyclic moieties of Q³ except forsubstituted C₁-C₁₅-alkyl moieties are unsubstituted or substituted withidentical or different groups Q^(3a) as defined and preferably definedherein; and wherein the substituted C₁-C₁₅-alkyl moieties of Q³ are orsubstituted with identical or different groups Q^(3c) as defined andpreferably defined herein.

Q^(3a) are the possible substituents for the aliphatic moieties of Q³except for substituted C₁-C₁₅-alkyl moieties.

According to one embodiment Q^(3a) is independently selected fromhalogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x),C₁-C₆-halogenalkylthio, S(O)_(m)—C₁-C₆-alkyl,S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl, CH(═O), C(═O)C₁-C₆-alkyl,C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂,CR′═NOR″, C₁-C₆-alkoxy C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, phenyl, phenoxy and five- toten-membered heterocycle, heteroaryl, heterocycloxy and heteryloxy;wherein in each case one or two CH₂ groups of the carbocycle andheterocycle may be replaced by a group independently selected from C(═O)and C(═S); wherein the heterocycle or heteroaryl contains one, two orthree heteroatoms selected from N, O and S; wherein the carbocyclic,heterocyclic, aryl, phenoxy, and heteroaryl groups are unsubstituted orsubstituted with 1, 2, 3, 4 or 5 substituents Q^(31a) selected from thegroup consisting of halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkylthio, S(O)_(m)—C₁-C₆-alkyl, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, CR′═NOR″, phenyl,phenoxy and five- to ten-membered heterocycle and heteroaryl; whereinthe heterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; and wherein the phenyl, phenoxy, heterocycleand heteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4or 5 substituents Q^(31a) selected from the group consisting of halogen,OH, CN, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, CN, CR′═NOR″ andC₁-C₄-halogenalkoxy; and wherein m, R^(x), R′ and R″ is defined asabove;

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from halogen, OH, CN, NO₂, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), CH(═O), C(═O)C₁-C₆-alkyl,C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl) or CR′═NOR″.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from OH, CN, CH(═O), C(═O)C₁-C₆-alkyl,C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl) such as CN, CHO, C(O)O(CH₃),CO₂NH(CH₃) or CO₂N(CH₃)₂.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from, S(O)₂—C₁-C₆-alkyl,S(O)₂—C₁-C₆-halogenalkyl, S(O)₂-aryl, such as SCH₃, SO₂CH₃, SO₂Ph.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH—SO₂—R^(x), such as NH(CH₃) N(CH₃)₂, NHSO₂CH₃, NHSO₂CF₃ or NHSO₂Ph.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,such as cyclopropyl or fully or partially halogenated cyclopropyl.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, such asOCF₃, OCHF₂, OCH₂F, OCCl₃, OCHCl₂ or OCH₂Cl, in particular OCF₃, OCHF₂,OCCl₃ or OCHCl₂.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from heterocycle, wherein the heterocycle is asaturated, two CH₂ groups are replaced by C(═O) and contains one N as aring member.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from aryl, wherein the aryl is substituted byhalogen selected from the group consisting of F, C, Br, CH₃, CHF₂, OCH₃,OCHF₂, OCF₃, CN or SO₂CH₃.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from halogen, OH, CN, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl and heterocycle, wherein the heterocyclocycle isa saturated and contains one N as a ring member.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from halogen, OH, CN, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl and heterocycle, wherein the heterocycle is asaturated, one CH₂ group is replaced by C(═O) and contains one N as aring member.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from halogen, OH, CN, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl and heterocycle, wherein the heretocyclocycle isa saturated, two CH₂ groups are replaced by C(═O) and contains one N asa ring member.

According to one preferred embodiment, Q^(3a) is in each caseindependently selected from halogen, OH, CN, C₁-C₆-alkoxy,C₁-C₆-halogenalkoxy, phenyl, aryl or heteroaryl; wherein the aryl andheteroaryl is substituted by halogen selected from the group consistingof F, C, Br, CH₃, CHF₂, OCH₃, OCHF₂, OCF₃, CN or SO₂CH₃.

According to one further preferred embodiment, Q^(3a) is in each caseindependently selected from halogen, phenyl, halogenphenyl andheteroaryl, wherein the halogenphenyl is substituted by halogen selectedfrom the group consisting of F, Cl and Br, in particular selected from Fand Cl.

According to one further preferred embodiment, Q^(3a) is in each caseindependently selected from halogen, CN, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₆-alkoxy, C₁-C₄-halogenalkoxy,C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio, phenyl, wherein the phenyl issubstituted by halogen selected from the group consisting of F, C and Bror by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy.

According to one further preferred embodiment, Q^(3a) is in each caseindependently selected from halogen and phenyl wherein the phenyl issubstituted by halogen selected from the group consisting of F, Cl andBr, in particular selected from F and Cl.

According to still another embodiment of formula I, Q^(3a) is apartially unsaturated three-, four-, five-, six-, seven-, eight-, nine-,or ten-membered carbocycle, in particular three-, four-, five- orsix-membered, wherein the carbocycle is unsubstituted or substituted bysubstituents Q^(3b) as defined below. According to one embodimentthereof, the carbocycle is unsubstituted.

According to still another embodiment of formula I, Q^(3a) is apartially unsaturated three-, four-, five-, six-, seven-, eight-, nine-,or ten-membered carbocycle or heterocycle, in particular three-, four-,five- or six-membered, wherein the heterocycle contains one, two, threeor four heteroatoms selected from N, O and S, and wherein the carbocycleand heterocycle are unsubstituted or substituted with substituentsQ^(3b) as defined below. According to one embodiment thereof, thecarbocycle or heterocycle is unsubstituted.

According to still a further embodiment, Q^(3a) is a saturated three-,four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle orheterocycle, in particular three-, four-, five- or six-membered, whereinthe heterocycle contains one, two, three or four heteroatoms selectedfrom N, O and S, and wherein the carbocycle and heterocycle areunsubstituted or substituted with substituents Q^(3b) as defined below.According to one embodiment thereof, the carbocycle or heterocycle isunsubstituted.

According to still another embodiment of formula I, Q^(3a) is asaturated three-, four-, five-, six-, seven-, eight-, nine-, orten-membered carbocycle, in particular three-, four-, five- orsix-membered, wherein the carbocycle is unsubstituted or substituted bysubstituents Q^(3b) as defined below. According to one embodimentthereof, the carbocycle is unsubstituted.

According to one embodiment, Q^(3a) is a 3-membered saturatedcarbocycle. According to one embodiment thereof, the carbocycle isunsubstituted, i.e. it does not carry any substituent Q³. According tostill another embodiment of formula I, it is substituted by Q³

According to one embodiment, Q^(3a) is a 3-membered saturatedcarbocycle, which is unsubstituted such as cyclopropyl.

According to one embodiment, Q^(3a) is a 3-membered saturatedcarbocycle, which is substituted by halogen, more specifically by F,such as C₃H₃F₂.

According to one embodiment, Q^(3a) is a 3-membered saturatedcarbocycle, which is substituted by halogen. More specifically by C,such as C₃H₃Cl₂.

According to one embodiment, Q^(3a) is a 4-membered saturatedcarbocycle. According to one embodiment thereof, the carbocycle isunsubstituted, i.e. it does not carry any substituent Q³. According tostill another embodiment of formula I, it is substituted by Q³

According to one embodiment, Q^(3a) is a 5-membered saturatedcarbocycle. According to one embodiment thereof, the carbocycle isunsubstituted, i.e. it does not carry any substituent Q^(3b). Accordingto still another embodiment of formula I, it is substituted by Q^(3b)

According to one embodiment, Q^(3a) is a 6-membered saturatedcarbocycle. According to one embodiment thereof, the carbocycle isunsubstituted, i.e. it does not carry any substituent Q^(3b). Accordingto still another embodiment of formula I, it is substituted by Q^(3b)

According to still another embodiment of formula I, Q^(3a) is apartially unsaturated three-, four-, five-, six-, seven-, eight-, nine-,or ten-membered heterocycle, in particular three-, four-, five- orsix-membered, wherein the heterocycle contains one, two, three or fourheteroatoms selected from N, O and S, and wherein the heterocycle isunsubstituted or substituted by substituents Q^(3b) as defined below.According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, Q^(3a) is asaturated three-, four-, five-, six-, seven-, eight-, nine-, orten-membered heterocycle, in particular three-, four-, five- orsix-membered, wherein the heterocycle contains one, two, three or fourheteroatoms selected from N, O and S, and wherein the heterocycle isunsubstituted or substituted by substituents Q^(3b) as defined below.According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, in the embodimentsof Q^(3a) described above, the heterocycle contains preferably one, twoor three, more specifically one or two heteroatoms selected from N, Oand S. More specifically, the hetereocycle contains one heteroatomselected from N, O and S. In particular, the heterocycle contains one ortwo, in particular one O.

According to one embodiment, Q^(3a) is a 4-membered saturatedheterocycle which contains 1 or 2 heteroatoms, in particular 1heteroatom, from the group consisting of N, O and S, as ring members.According to one embodiment, the heterocycle contains one O asheteroatom. For example, the formed heterocycle is oxetane. According toone embodiment thereof, the heterocycle is unsubstituted, i.e. it doesnot carry any substituent Q³. According to still another embodiment offormula I, it is substituted by Q³

According to still another embodiment of formula I, Q^(3a) is a5-membered saturated heterocycle which contains 1, 2 or 3, in particular1 or 2, heteroatoms from the group consisting of N, O and S, as ringmembers. According to one embodiment, the heterocycle contains one O asheteroatom. According to one embodiment thereof, the heterocycle isunsubstituted, i.e. it does not carry any substituent Q³. According tostill another embodiment of formula I, it is substituted by Q^(3b).

According to still another embodiment of formula I, Q^(3a) is a6-membered saturated heterocycle which contains 1, 2 or 3, in particular1 or 2, heteroatoms from the group consisting of N, O and S as ringmembers. According to one embodiment thereof, the heterocycle isunsubstituted, i.e. it does not carry any substituent Q^(3b). Accordingto still another embodiment of formula I, it is substituted by Q^(3b).According to one specific embodiment thereof, said 6-membered saturatedheterocycle contains 1 or 2, in particular 1, heteroatom(s) 0. Accordingto one embodiment thereof, the respective 6-membered heterocycle isunsubstituted, i.e. it does not carry any substituent Q^(3b). Accordingto still another embodiment of formula I, it is substituted by Q^(3b).

Q^(3b) are the possible substituents for the carbocycle, heterocycle,heteroaryl and aryl moieties of Q³.

Q^(3b) according to the invention is independently selected fromhalogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₄-alkyl,C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, C₁-C₄-alkoxy,C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, S(O)_(m)—C₁-C₆-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, phenoxy and five- to ten-memberedheterocycle, heteroaryl, heterocycloxy, heteryloxy; wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; wherein the phenyl, phenoxy, heterocycle andheteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5substituents Q^(31b) selected from the group consisting of halogen, OH,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,CR′═NOR″; phenyl, phenoxy and five- to ten-membered heterocycle andheteroaryl; wherein the heterocycle or heteroaryl contains one, two orthree heteroatoms selected from N, O and S; and wherein the phenyl,phenoxy, heterocycle and heteroaryl groups are unsubstituted orsubstituted with 1, 2, 3, 4 or 5 substituents Q^(31b) selected from thegroup consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, CN, CR′═NOR″ and C₁-C₄-halogenalkoxy; and wherein R′, R″and R^(x) are defined as above;

According to one embodiment thereof Q^(3b) is independently selectedfrom halogen, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl andC₁-C₄-halogenalkoxy, in particular halogen, C₁-C₄-alkyl andC₁-C₄-alkoxy. Specifically, Q^(3b) is independently selected from F, Cl,CN, CH₃, CHF₂, CF₃OCH₃ and halogenmethoxy.

According to one preferred embodiment, Q^(3b) is in each caseindependently selected from halogen, OH, CN, SH, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkylthioand S(O)_(m)—C₁-C₆-alkyl. According to one further preferred embodiment,Q^(3b) is in each case independently selected from halogen,C₁-C₆-alkoxy, C₁-C₆-halogenalkyl, C₁-C₆-halogenalkoxy andS(O)_(m)—C₁-C₆-alkyl. According to one further particular embodiment,Q^(3b) is in each case independently selected from halogen such as Cl,Br, F. According to one further particular embodiment, Q^(3b) is in eachcase independently selected from C₁-C₆-alkyl, such as methyl and ethyl.According to one further particular embodiment, Q^(3b) is in each caseindependently selected from halogen, such as F, Cl and Br. According toone further particular embodiment, Q^(3b) is in each case independentlyselected from C₁-C₆-alkoxy, such as OCH₃. According to one furtherparticular embodiment, Q^(3b) is in each case independently selectedfrom C₁-C₄-halogenalkoxy, such as OCHF₂ and OCF₃. According to onefurther particular embodiment, Q³ is in each case independently selectedfrom S(O)_(m)—C₁-C₆-alkyl such as SO₂CH₃.

Q^(3c) are the possible substituents for the substituted C₁-C₁₅-alkylmoieties of Q³.

Q^(3c) according to the invention is independently selected fromhalogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₄-alkoxy,C₁-C₄-halogenalkoxy, C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio,C₁-C₆-halogenalkylthio, S(O)_(m)—C₁-C₆-alkyl,S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl, CH(═O), C(═O)C₁-C₆-alkyl,C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂,CR′═NOR″, a saturated or partially unsaturated three-, four-, five-,six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle,aryl and five-, six- or ten-membered heteroaryl, heterocycloxy,heteryloxy; wherein in each case one or two CH₂ groups of the carbocycleand heterocycle may be replaced by a group independently selected fromC(═O) and C(═S); wherein the heterocycle and heteroaryl containindependently one, two, three or four heteroatoms selected from N, O andS; wherein the carbocyclic, heterocyclic, aryl, phenoxy and heteroarylgroups are independently unsubstituted or carry one, two, three, four orfive substituents Q^(31c) selected from the group consisting of shalogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x),C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy,C₁-C₄-halogenalkoxy, S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″; phenyl, phenoxyand five- to ten-membered heterocycle and heteroaryl; wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; and wherein the carbocyclic, heterocyclic,phenyl, phenoxy, heterocycle and heteroaryl groups are unsubstituted orsubstituted with 1, 2, 3, 4 or 5 substituents Q^(31c) selected from thegroup consisting of halogen, OH, CN, NO₂, SH, NH, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy and S(O)_(m)—C₁-C₆-alkyl; wherein m,R^(x), R′ and R″ is as defined above;

According to still another embodiment of formula I, Q³ is C₁-C₆-alkylsuch as CH₃, C₂H₅, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl,n-pentyl or i-pentyl which is substituted by at least one group R⁴,which independently of one another are selected from: halogen, OH, CN,NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl), NH—SO₂—R^(x), C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio,S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl,CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, a saturated or partially unsaturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedcarbocycle or heterocycle, aryl and five-, six- or ten-memberedheteroaryl, heterocycloxy, heteryloxy; wherein in each case one or twoCH₂ groups of the carbocycle and heterocycle may be replaced by a groupindependently selected from C(═O) and C(═S); wherein the heterocycle andheteroaryl contain independently one, two, three or four heteroatomsselected from N, O and S; wherein the carbocyclic, heterocyclic, aryl,phenoxy and heteroaryl groups are independently unsubstituted or carryone, two, three, four or five substituents Q³¹ selected from the groupconsisting of s halogen, OH, CN, NO₂, SH, NH, N H(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″;phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the carbocyclic,heterocyclic, phenyl, phenoxy, heterocycle and heteroaryl groups areunsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q^(31c)selected from the group consisting of halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy andS(O)_(m)—C₁-C₆-alkyl;

According to still another embodiment of formula I, Q³ is CH₃ which issubstituted by at least one group Q^(3c), which independently of oneanother are selected from: halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio,S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl,CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, a saturated or partially unsaturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedcarbocycle or heterocycle, aryl and five-, six- or ten-memberedheteroaryl, heterocycloxy, heteryloxy; wherein in each case one or twoCH₂ groups of the carbocycle and heterocycle may be replaced by a groupindependently selected from C(═O) and C(═S); wherein the heterocycle andheteroaryl contain independently one, two, three or four heteroatomsselected from N, O and S; wherein the carbocyclic, heterocyclic, aryl,phenoxy and heteroaryl groups are independently unsubstituted or carryone, two, three, four or five substituents Q^(31c) selected from thegroup consisting of s halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″;phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the carbocyclic,heterocyclic, phenyl, phenoxy, heterocycle and heteroaryl groups areunsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q^(31c)selected from the group consisting of halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy andS(O)_(m)—C₁-C₆-alkyl;

According to still another embodiment of formula I, Q³ is Et which issubstituted by at least one group Q^(3c), which independently of oneanother are selected from: halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio,S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl,CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, a saturated or partially unsaturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedcarbocycle or heterocycle, aryl and five-, six- or ten-memberedheteroaryl, heterocycloxy, heteryloxy; wherein in each case one or twoCH₂ groups of the carbocycle and heterocycle may be replaced by a groupindependently selected from C(═O) and C(═S); wherein the heterocycle andheteroaryl contain independently one, two, three or four heteroatomsselected from N, O and S; wherein the carbocyclic, heterocyclic, aryl,phenoxy and heteroaryl groups are independently unsubstituted or carryone, two, three, four or five substituents Q³¹ selected from the groupconsisting of s halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″;phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the carbocyclic,heterocyclic, phenyl, phenoxy, heterocycle and heteroaryl groups areunsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q^(31c)selected from the group consisting of halogen, OH, CN, NO₂, SH, NH,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy andS(O)_(m)—C₁-C₆-alkyl;

According to still another embodiment of formula I, Q³ is Pr which issubstituted by at least one group Q³, which independently of one anotherare selected from: halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio,S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl,CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, a saturated or partially unsaturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedcarbocycle or heterocycle, aryl and five-, six- or ten-memberedheteroaryl, heterocycloxy, heteryloxy; wherein in each case one or twoCH₂ groups of the carbocycle and heterocycle may be replaced by a groupindependently selected from C(═O) and C(═S); wherein the heterocycle andheteroaryl contain independently one, two, three or four heteroatomsselected from N, O and S; wherein the carbocyclic, heterocyclic, aryl,phenoxy and heteroaryl groups are independently unsubstituted or carryone, two, three, four or five substituents Q³ selected from the groupconsisting of s halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″;phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the carbocyclic,heterocyclic, phenyl, phenoxy, heterocycle and heteroaryl groups areunsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q^(31c)selected from the group consisting of halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy andS(O)L-C₁-C₆-alkyl;

According to still another embodiment of formula I, Q³ is iPr which issubstituted by at least one group Q^(3c), which independently of oneanother are selected from: halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio,S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl,CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, a saturated or partially unsaturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedcarbocycle or heterocycle, aryl and five-, six- or ten-memberedheteroaryl, heterocycloxy, heteryloxy; wherein in each case one or twoCH₂ groups of the carbocycle and heterocycle may be replaced by a groupindependently selected from C(═O) and C(═S); wherein the heterocycle andheteroaryl contain independently one, two, three or four heteroatomsselected from N, O and S; wherein the carbocyclic, heterocyclic, aryl,phenoxy and heteroaryl groups are independently unsubstituted or carryone, two, three, four or five substituents Q^(31c) selected from thegroup consisting of s halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″;phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the carbocyclic,heterocyclic, phenyl, phenoxy, heterocycle and heteroaryl groups areunsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q^(31c)selected from the group consisting of halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy andS(O)_(m)—C₁-C₆-alkyl;

According to still another embodiment of formula I, Q³ is butyl which issubstituted by at least one group Q^(3c), which independently of oneanother are selected from: halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio,S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl,CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, a saturated or partially unsaturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedcarbocycle or heterocycle, aryl and five-, six- or ten-memberedheteroaryl, heterocycloxy, heteryloxy; wherein in each case one or twoCH₂ groups of the carbocycle and heterocycle may be replaced by a groupindependently selected from C(═O) and C(═S); wherein the heterocycle andheteroaryl contain independently one, two, three or four heteroatomsselected from N, O and S; wherein the carbocyclic, heterocyclic, aryl,phenoxy and heteroaryl groups are independently unsubstituted or carryone, two, three, four or five substituents Q^(31c) selected from thegroup consisting of s halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″;phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the carbocyclic,heterocyclic, phenyl, phenoxy, heterocycle and heteroaryl groups areunsubstituted or substituted with 1, 2, 3, 4 or 5 substituents Q^(31c)selected from the group consisting of halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy andS(O)_(m)—C₁-C₆-alkyl;

According to still another embodiment of formula I, Q³ is CH₂CN.

According to still another embodiment of formula I, Q³ is CH₂OH.

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl-C₁-C₆-alkoxy, in particular C₁-C₇-alkyl-C₁-C₄-alkoxy, morespecifically C₁-C₄-alkyl-C₁-C₂-alkoxy such as CH₂OCH₃, CH₂CH₂OCH₃CH₂CH₂OCH₂CH₃, CH₂CH₂, CH₂OCH₃CH₂CH₂, CH₂O CH₂CH₃,

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl-C₁-C₆-halogenalkoxy, in particularC₁-C₇-alkyl-C₁-C₄-halogenalkoxy, more specificallyC₁-C₄-alkyl-C₁-C₂-halogenalkoxy such as CH₂OCF₃, CH₂CH₂OCF₃, CH₂OCHF₂,CH₂OCH₂F, CH₂OCCl₃, CH₂OCHCl₂ or CH₂OCH₂Cl, in particular CH₂OCF₃,CH₂OCHF₂, CH₂OCCl₃ or CH₂OCHCl₂.

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl-C₁-C₆-halogenalkylthio, in particularC₁-C₁₅-alkyl-C₁-C₄-halogenalkylthio, more specificallyC₁-C₄-alkyl-C₁-C₂-halogenalkylthio such as CH₂SCF₃, CH₂SCHF₂, CH₂SCH₂F,CH₂SCCl₃, CH₂SCHCl₂ or CH₂SCH₂Cl, in particular CH₂SCF₃, CH₂SCHF₂,CH₂SCCl₃ or CH₂SCHCl₂.

According to a further specific embodiment of formula I, Q³ isC₁-C₅-alkyl-CH(═O), C₁-C₁₅-alkyl-C(═O)C₁-C₆-alkyl,C₁-C₁₅-alkyl-C(═O)O(C₁-C₆-alkyl), C₁-C₁₅-alkyl-C(═O)NH(C₁-C₆-alkyl) orC₁-C₁₅-alkyl-C(═O)N(C₁-C₆-alkyl)₂, especially CH₂CH(═O),CH₂C(═O)C₁-C₆-alkyl, CH₂C(═O)O(C₁-C₆-alkyl), CH₂C(═O)NH(C₁-C₆-alkyl) orCH₂C(═O)N(C₁-C₆-alkyl)₂ wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl-NH(C₁-C₄-alkyl), C₁-C₁₅-alkyl-N(C₁-C₄-alkyl)₂,C₁-C₁₅-alkyl-NH(C(═O)C₁-C₄-alkyl) or C₁-C₁₅-alkyl-N(C(═O)C₁-C₄-alkyl)₂,wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl, n-butyl, i-butyl,tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl-S(O)—C₁-C₆-alkyl, wherein alkyl is CH₃, C₂H₅, n-propyl,i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl-S(O)₂—C₁-C₆-alkyl, wherein alkyl is CH₃, C₂H₅, n-propyl,i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, Q³ isC₁-C₅-alkyl-S(O)₂—C₁-C₆-halogenalkyl, wherein halogenalkyl is CF₃ orCHF₂ and z is 0, 1, 2 or 3.

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl-S(O)₂-aryl, wherein the aryl or phenyl moiety in each caseis independently unsubstituted or carry one, two, three, four or fivesubstituents selected from the group consisting of halogen, OH, CN, NO₂,SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkylthio, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy andS(O)_(z)—C₁-C₆-alkyl, in particular F, C, Br, CH₃, OCH₃, CF₃, CHF₂,OCHF₂, OCF₃.

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl-NH—SO₂—R^(x) wherein R^(x) is C₁-C₄-alkyl,C₁-C₄-halogenalkyl, unsubstituted aryl or aryl that is substituted byone, two, three, four or five substituents R^(x2) independently selectedfrom C₁-C₄-alkyl, halogen, OH, CN, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, orC₁-C₄-halogenalkoxy, such as CH₂NHSO₂CF₃ or CH₂NHSO₂CH₃.

According to still another embodiment of formula I, Q³ is selected fromC₁-C₁₅-alkyl which is substituted, a saturated three-, four-, five-,six-, seven-, eight-, nine-, or ten-membered carbocycle, in particularthree-, four-, five- or six-membered, wherein the carbocycle isunsubstituted or substituted by substituents Q^(3b) as defined below.According to one embodiment thereof, the carbocycle is unsubstituted.

According to one embodiment, Q³ is selected from C₁-C₁₅-alkyl,especially CH₂ which is substituted by a 3-membered saturatedcarbocycle. According to one embodiment thereof, the carbocycle isunsubstituted, i.e. it does not carry any substituent Q³. According tostill another embodiment of formula I, it is substituted by Q³

According to one embodiment, Q³ is selected from C₁-C₁₅-alkyl,especially CH₂ which is substituted by a 4-membered saturatedcarbocycle. According to one embodiment thereof, the carbocycle isunsubstituted, i.e. it does not carry any substituent Q³. According tostill another embodiment of formula I, it is substituted by Q³

According to one embodiment, Q³ is selected from C₁-C₁₅-alkyl,especially CH₂ which is substituted by a 5-membered saturatedcarbocycle. According to one embodiment thereof, the carbocycle isunsubstituted, i.e. it does not carry any substituent Q³. According tostill another embodiment of formula I, it is substituted by Q³

According to one embodiment, Q³ is selected from C₁-C₁₅-alkyl,especially CH₂ which is substituted by a 6-membered saturatedcarbocycle. According to one embodiment thereof, the carbocycle isunsubstituted, i.e. it does not carry any substituent Q³. According tostill another embodiment of formula I, it is substituted by Q³

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 4-membered saturatedheterocycle which contains 1 or 2 heteroatoms, in particular 1heteroatom, from the group consisting of N, O and S, as ring members.According to one embodiment, the heterocycle contains one O asheteroatom. For example, the formed heterocycle is oxetane. According toone embodiment thereof, the heterocycle is unsubstituted, i.e. it doesnot carry any substituent Q³. According to still another embodiment offormula I, it is substituted by Q³

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatomsfrom the group consisting of N, O and S, as ring members. According toone embodiment, the heterocycle contains one O as heteroatom. Accordingto one embodiment thereof, the heterocycle is unsubstituted, i.e. itdoes not carry any substituent Q³. According to still another embodimentof formula I, it is substituted by Q^(3b).

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 6-membered saturatedheterocycle which contains 1, 2 or 3, in particular 1 or 2, heteroatomsfrom the group consisting of N, O and S as ring members. According toone embodiment thereof, the heterocycle is unsubstituted, i.e. it doesnot carry any substituent Q^(3b). According to still another embodimentof formula I, it is substituted by Q^(3b). According to one specificembodiment thereof, said 6-membered saturated heterocycle contains 1 or2, in particular 1, heteroatom(s) O. According to one embodimentthereof, the respective 6-membered heterocycle is unsubstituted, i.e. itdoes not carry any substituent Q³. According to still another embodimentof formula I, it is substituted by Q³

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheterocycle which contains one N as ring member and optionally one ortwo groups CH₂ are replaced by C(═O).

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatomsfrom the group consisting of N, O and S as ring members. According toone embodiment thereof, the heteroaryl is unsubstituted, i.e. it doesnot carry any substituent Q³. According to still another embodiment offormula I, it is substituted by Q³

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheteroaryl which contains one N as ring member. According to oneembodiment thereof, the heteroaryl is unsubstituted, i.e. it does notcarry any substituent Q^(3b). According to still another embodiment offormula I, it is substituted by Q³

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheteroaryl which contains two N as ring members. According to oneembodiment thereof, the heteroaryl is unsubstituted, i.e. it does notcarry any substituent Q^(3b). According to still another embodiment offormula I, it is substituted by Q³

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheteroaryl which contains three N as ring members. According to oneembodiment thereof, the heteroaryl is unsubstituted, i.e. it does notcarry any substituent Q^(3b). According to still another embodiment offormula I, it is substituted by Q³ According to one specific embodimentthereof, said 5-membered saturated heterocycle contains 1 or 2, inparticular 1, heteroatom(s) O.

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheteroaryl which contains one S as ring member. According to oneembodiment thereof, the heteroaryl is unsubstituted, i.e. it does notcarry any substituent Q³⁴. According to still another embodiment offormula I, it is substituted by Q^(3b)

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheteroaryl which contains one S and one N as ring members. According toone embodiment thereof, the heteroaryl is unsubstituted, i.e. it doesnot carry any substituent Q^(3b). According to still another embodimentof formula I, it is substituted by Q^(3b)

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheteroaryl which contains one S and two N as ring members. According toone embodiment thereof, the heteroaryl is unsubstituted, i.e. it doesnot carry any substituent Q^(3b). According to still another embodimentof formula I, it is substituted by Q^(3b)

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheteroaryl which contains one oxygen and one N as ring members.According to one embodiment thereof, the heteroaryl is unsubstituted,i.e. it does not carry any substituent Q³. According to still anotherembodiment of formula I, it is substituted by Q^(3b).

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 5-membered saturatedheteroaryl which contains one oxygen and two N as ring members.According to one embodiment thereof, the heteroaryl is unsubstituted,i.e. it does not carry any substituent Q^(3b). According to stillanother embodiment of formula I, it is substituted by Q^(3b).

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 6-membered saturatedheteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatomsfrom the group consisting of N, O and S as ring members. According toone embodiment thereof, the heteroaryl is unsubstituted, i.e. it doesnot carry any substituent Q^(3b). According to still another embodimentof formula I, it is substituted by Q^(3b)

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 6-membered saturatedheteroaryl which one N as ring member. According to one embodimentthereof, the heteroaryl is unsubstituted, i.e. it does not carry anysubstituent Q^(3b). According to still another embodiment of formula I,it is substituted by Q^(3b)

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 6-membered saturatedheteroaryl which two N as ring members. According to one embodimentthereof, the heteroaryl is unsubstituted, i.e. it does not carry anysubstituent Q^(3b) According to still another embodiment of formula I,it is substituted by Q^(3b)

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 10-membered saturatedheteroaryl which contains 1, 2 or 3, in particular 1 or 2, heteroatomsfrom the group consisting of N, O and S as ring members. According toone embodiment thereof, the heteroaryl is unsubstituted, i.e. it doesnot carry any substituent Q^(3b)

According to still another embodiment of formula I, it is substituted byQ^(3b). According to one specific embodiment thereof, said 10-memberedsaturated heterocycle contains 1 or 2, in particular 1, heteroatom(s) N.

According to a further specific embodiment of formula I, Q³ isC₁-C₁₅-alkyl, especially CH₂ substituted by a 10-membered saturatedheteroaryl which one N as ring members. According to one embodimentthereof, the heteroaryl is unsubstituted, i.e. it does not carry anysubstituent Q^(3b) According to still another embodiment of formula I,it is substituted by Q^(3b)

According to still another embodiment of formula I, Q³ is CH₂substituted by a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl,pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl,pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl,imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl,oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl,thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl,isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.

According to still another embodiment of formula I, Q³ is CH₂substituted by a 6-membered heteroaryl, such as pyridin-2-yl,pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl,pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected from OH, CN, NO₂, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl),C(═O)NH(C₁-C₆-alkyl) or CR′═NOR″.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected from OH, CN, CH(═O), C(═O)C₁-C₆-alkyl,C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl) such as CN, CHO, C(O)CH₃,C(O)O(CH₃), CO₂NH(CH₃) or CO₂N(CH₃)₂.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected from C₁-C₆-halogenalkylthio, S(O)—C₁-C₆-alkyl,S(O)₂—C₁-C₆-alkyl, S(O)₂—C₁-C₆-halogenalkyl, S(O)_(z)-aryl, such asSCH₃, SO₂CH₃, SO₂Ph.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected from NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), such as 15NH(CH₃) N(CH₃)₂ or NHSO₂CH₃, NHSO₂CF₃.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected from C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,such as cyclopropyl or fully or partially halogenated cyclopropyl.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected C₁-C₆-halogenalkoxy, such as OCF₃, OCHF₂, OCH₂F,OCCl₃, OCHCl₂ or OCH₂Cl, in particular OCF₃, OCHF₂, OCCl₃ or OCHCl₂.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected from heterocycle, wherein the heterocycle is asaturated, two CH₂ groups are replaced by C(═O) and contains one N as aring member.

According to one prefer embodiment, Q³ is unsubstituted 5- or 6-memberedheteroaryl.

According to still a further embodiment, R⁴ is 5- or 6-memberedheteroaryl substituted by halogen selected from the group consisting ofF, C, Br, CH₃, CHF₂, OCH₃, OCHF₂, OCF₃, CN or SO₂CH₃.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected from OH, CN, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl and heterocycle, wherein the heterocycle is asaturated and contains one N as a ring member.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected from OH, CN, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl and heterocycle, wherein the heterocycle is asaturated, one CH₂ group is replaced by C(═O) and contains one N as aring member.

According to one preferred embodiment, Q^(3c) is in each caseindependently selected from OH, CN, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl and heterocycle, wherein the heretocyclocycle isa saturated, two CH₂ groups are replaced by C(═O) and contains one N asa ring member.

Particularly preferred embodiments of Q³ according to the invention arein Table Q3 below, wherein each line of lines Q³-1 to Q³-163 correspondsto one particular embodiment of the invention, wherein Q³-1 to Q³-163are also in any combination with one another a preferred embodiment ofthe present invention:

No. Q³ Q3-1 CF₃ Q3-2 CHF₂ Q3-3 CH₂CH₂OCH₃ Q3-4 CH₂OCH₂F Q3-5 CH₂OCHF₂Q3-6 CH₂OCF₃ Q3-7 CH₂OCF₂CHF₂ Q3-8 CH₂SOMe Q3-9 CH₂SO₂Me Q3-10 CH₂NMe₂Q3-11 CH₂NSO₂CF₃ Q3-12 CH₂NSO₂CH₃ Q3-13 CH₂cPr Q3-14 C₆H₅ Q3-15—CH₂—C₆H₅ Q3-16 —CH₂—C₆H₄-4-F Q3-17 —CH₂—C₆H₄-4-CH₃ Q3-18—CH₂—C₆H₄-3-CH₃ Q3-19 —CH₂—C₆H₄-2-CH₃ Q3-20 —CH(CH₃)—C₆H₅ Q3-21CH(CH₃)—C₆H₄-4-F Q3-22 CH(CH₃)—C₆H₄-4-CH₃ Q3-23 CH(CH₃)—C₆H₄-3-CH₃ Q3-24CH(CH₃)—C₆H₄-2-CH₃ Q3-25

Q3-26

Q3-27

Q3-28

Q3-29

Q3-30

Q3-31

Q3-32

Q3-33

Q3-34

Q3-35 2-py Q3-36 3-py Q3-37

Q3-38

Q3-39

Q3-40

Q3-41

Q3-42

Q3-43

Q3-44

Q3-45

Q3-46

Q3-47

Q3-48

Q3-49

Q3-50

Q3-51

Q3-52

Q3-53

Q3-54

Q3-55

Q3-56

Q3-57

Q3-58

Q3-59

Q3-60

Q3-61

Q3-62

Q3-63

Q3-64

Q3-65

Q3-66

Q3-67

Q3-68

Q3-69

Q3-70

Q3-71

Q3-72

Q3-73

Q3-74

Q3-75

Q3-76

Q3-77

Q3-78

Q3-79

Q3-80

Q3-81

Q3-82

Q3-83

Q3-84

Q3-85

Q3-86

Q3-87

Q3-88

Q3-89

Q3-90

Q3-91 COCH₃ Q3-92 COCH₂CH₃ Q3-93 COCH₂CH₂CH₃ Q3-94 CO(CH₂)₃CH₃ Q3-95CO(CH₂)₄CH₃ Q3-96 CO(CH₂)₅CH₃ Q3-97 CO(CH₂)₆CH₃ Q3-98 COCCl₃ Q3-99COCH₂Cl Q3-100 COCH₂—N(CH₃)₂ Q3-101 COPh Q3-102 COCH₂Ph Q3-103COCH₂Ph-4-F Q3-104 COCH₂Ph-4-CH₃ Q3-105 COCH₂Ph-3-CH₃ Q3-106COCH₂Ph-2-CH₃ Q3-107 COCH(CH₃)Ph Q3-108 COCH(CH₃)4-F Q3-109COCH(CH₃)-4-CH₃ Q3-110 COCH(CH₃)-3-CH₃ Q3-111 COCH(CH₃)-3-CH₃ Q3-112

Q3-113

Q3-114

Q3-115

Q3-116

Q3-117

Q3-118

Q3-119

Q3-120

Q3-121

Q3-122

Q3-123

Q3-124

Q3-125

Q3-126

Q3-127

Q3-128

Q3-129

Q3-130

Q3-131

Q3-132

Q3-133

Q3-134

Q3-135

Q3-136

Q3-137

Q3-138

Q3-139

Q3-140

Q3-141

Q3-142

Q3-143

Q3-144

Q3-145

Q3-146

Q3-147

Q3-148

Q3-149

Q3-150

Q3-151

Q3-152

Q3-153

Q3-154

Q3-155

Q3-156

Q3-157

Q3-158

Q3-159

Q3-160

Q3-161

Q3-162

Q3-163

Q⁴ is in each case independently selected from hydrogen, OH, CH(O),C(O)C₁-C₆-alkyl, C(═O)C₂-C₆-alkenyl, C(═O)C₃-C₆-cycloalkyl,C(═O)O(C₁-C₆-alkyl), C(═O)O(C₂-C₆-alkenyl), C(═O)O(C₂-C₆-alkynyl),C(═O)O(C₃-C₆-cycloalkyl), C(═O)NH(C₁-C₆-alkyl), C(═O)NH(C₂-C₆-alkenyl),C(═O)NH(C₂-C₆-alkynyl), C(═O) NH(C₃-C₆-cycloalkyl),C(═O)N(C₁-C₆-alkyl)₂, C(═O)N(C₂-C₆-alkenyl)₂, C(═O)N(C₂-C₆-alkynyl)₂,C(═O)N(C₃-C₆-cycloalkyl)₂, CH(═S), C(═S)C₁-C₆-alkyl, C(═S)C₂-C₆-alkenyl,C(═S)C₂-C₆-alkynyl, C(═S)C₃-C₆-cycloalkyl, C(═S)O(C₁-C₆-alkyl),C(═S)O(C₂-C₆-alkenyl), C(═S)O(C₂-C₆-alkynyl), C(═S)O(C₃-C₆-cycloalkyl),C(═S)NH(C₁-C₆-alkyl), C(═S)NH(C₂-C₆-alkenyl), C(═S)NH(C₂-C₆-alkynyl),C(═S)NH(C₃-C₆-cycloalkyl), C(═S)N(C₁-C₆-alkyl)₂, C(═S)N(C₂-C₆-alkenyl)₂,C(═S)N(C₂-C₆-alkynyl)₂, C(═S)N(C₃-C₆-cycloalkyl)₂, C₁-C₆-alkyl,C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, OR, C₁-C₆-alkylthio,C₁-C₆-halogenalkylthio, C₂-C₆-alkenyl, C₂-C₆-halogenalkenylC₂-C₆-alkynyl, C₂-C₆-halogenalkynyl, S(O)_(m)—C₁-C₆-alkyl,S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)—C₁-C₆-alkoxy, S(O)—C₁-C₆-alkenyl,S(O)_(m)—C₂-C₆-alkynyl, S(O)_(m)-aryl, SO₂—NH(C₁-C₆-alkyl),SO₂—NH(C₁-C₆-halogenalkyl), SO₂—NH-aryl, tri-(C₁-C₆ alkyl)silyl anddi-(C₁-C₆ alkoxy)phosphoryl), five- or six-membered heteroaryl and aryl;wherein the heteroaryl contains one, two or three heteroatoms selectedfrom N, O and S; wherein the aryl groups are unsubstituted or carry one,two, three, four or five substituents selected from the group consistingof CN, halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy; wherein n andR^(Y) is C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-halogenalkenyl, C₁-C₆-alkynyl, C₂-C₆-halogenalkynyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, phenyl andphenyl-C₁-C₆-alkyl; wherein the phenyl groups are unsubstituted or carryone, two, three, four or five substituents selected from the groupconsisting of CN, halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;Q^(4a) is the substituent of the acyclic moieties of Q⁴. The acyclicmoieties of Q⁴ are not further substituted or carry one, two, three orup to the maximum possible number of identical or different groupsQ^(4a) which independently of one another are selected from halogen, OH,CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,C₃-C₆-halogencycloalkyl, C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy,C₁-C₆-alkylthio, five- or six-membered heteroaryl, aryl and phenoxy,wherein the heteroaryl, aryl and phenoxy group is unsubstituted orcarries one, two, three, four or five substituents selected from thegroup consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;Q⁴ is the subtituyend of carbocyclic, phenyl, heterocyclic andheteroaryl moieties of Q⁴. The carbocyclic, phenyl, heterocyclic andheteroaryl moieties of Q⁴ are not further substituted or carry one, two,three, four, five or up to the maximum number of identical or differentgroups Q^(4b) which independently of one another are selected fromhalogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy andC₁-C₆-alkylthio.

According to one embodiment of formula I, Q⁴ is H.

According to still another embodiment of formula I, Q⁴ is OH.

According to a further specific embodiment of formula I, Q⁴ is CH(═O).

According to a further specific embodiment of formula I, Q⁴ isC(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl) orC(═O)N(C₁-C₆-alkyl)₂, wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, Q⁴ isC(═O)C₂-C₆-alkenyl, C(═O)O(C₂-C₆-alkenyl), C(═O)NH(C₂-C₆-alkenyl) orC(═O)N(C₂-C₆-alkenyl)₂), wherein alkenyl is CH═CH₂, CH₂CH═CH₂.

According to a further specific embodiment of formula I, Q⁴ isC(═O)C₂-C₆-alkynyl, C(═O)O(C₂-C₆-alkynyl), C(═O)NH(C₂-C₆-alkynyl) orC(═O)N(C₂-C₆-alkynyl)₂, wherein alkynyl is C≡CH, CH₂C CH.

According to a further specific embodiment of formula I, Q⁴ isC(═O)C₃-C₆-cycloalkyl, C(═O)O(C₃-C₆-cycloalkyl),C(═O)NH(C₃-C₆-cycloalkyl) or C(═O)N(C₃-C₆-cycloalkyl)₂, whereincycloalkyl is cyclopropyl (C₃H₇) or cyclobutyl (C₄H₉).

According to a further specific embodiment of formula I, Q⁴ is CH(═S).

According to a further specific embodiment of formula I, Q⁴ isC(═S)C₁-C₆-alkyl, C(═S)O(C₁-C₆-alkyl), C(═S)NH(C₁-C₆-alkyl) orC(═S)N(C₁-C₆-alkyl)₂, wherein alkyl is CH₃, C₂H₅, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, Q⁴ isC(═S)C₂-C₆-alkenyl, C(═S)O(C₂-C₆-alkenyl), C(═S)NH(C₂-C₆-alkenyl) orC(═S)N(C₂-C₆-alkenyl)₂, wherein alkenyl is CH═CH₂, CH₂CH═CH₂.

According to a further specific embodiment of formula I, Q⁴ isC(═S)O(C₂-C₆-alkynyl), C(═S)NH(C₂-C₆-alkynyl) or C(═S)N(C₂-C₆-alkynyl),wherein alkynyl is C≡CH, CH₂C≡CH.

According to a further specific embodiment of formula I, Q⁴ isC(═S)C₃-C₆-cycloalkyl, C(═S)O(C₃-C₆-cycloalkyl) orC(═S)N(C₃-C₆-cycloalkyl)₂, wherein cycloalkyl is cyclopropyl (C₃H₇) orcyclobutyl (C₄H₉).

According to still another embodiment of formula I, Q⁴ is C₁-C₆-alkyl,such as CH₃, C₂H₅, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl,n-pentyl or i-pentyl.

According to still another embodiment of formula I, Q⁴ is C₁-C₆-alkyl,in particular C₁-C₄-alkyl, such as CH₃, C₂H, n-propyl, i-propyl.

According to still another embodiment of formula I, Q⁴ isC₁-C₆-halogenalkyl, in particular C₁-C₄-halogenalkyl, such as CF₃, CCl₃,FCH₂, ClCH₂, F₂CH, C₂CH, CF₃CH₂, CCl₃CH₂ or CF₂CHF₂.

According to still another embodiment of formula I Q⁴ isC₃-C₆-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I, Q⁴ isC₃-C₆-halogencycloalkyl. In a special embodiment Q⁴¹ is fully orpartially halogenated cyclopropyl, such as 1-F-cyclopropyl,1-Cl-cyclopropyl, 1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl.

According to still another embodiment of formula I, Q⁴ is C₁-C₄-alkoxyand C₁-C₄-halogenalkoxy, in particular C₁-C₃-alkoxy,C₁-C₃-halogenalkoxy, such as CH₂OCH₃, CH₂OCF₃ or CH₂OCHF₂.

According to a further specific embodiment of formula I, Q⁴ is ORwherein R is C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, phenyl andphenyl-C₁-C₆-alkyl; wherein the phenyl groups are unsubstituted or carryone, two, three, four or five substituents selected from the groupconsisting of CN, halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;

According to a further specific embodiment of formula I, Q⁴ is ORwherein R is C₁-C₆-alkyl, in particular C₁-C₄-alkyl, more specificallyC₁-C₂-alkyl. Q⁴ is such as OCH₃ or OCH₂CH₃.

According to a further specific embodiment of formula I, Q⁴ is ORwherein R is C₁-C₆-halogenalkyl, in particular C₁-C₄-halogenalkyl, morespecifically C₁-C₂-halogenalkyl. Q⁴ is such as OCF₃, OCHF₂, OCH₂F,OCCl₃, OCHCl₂ or OCH₂Cl, in particular OCF₃, OCHF₂, OCCl₃ or OCHCl₂.

According to a further specific embodiment of formula I, Q⁴ is ORwherein R C₂-C₆-alkenyl, in particular C₂-C₄-alkenyl, more specificallyC₁-C₂-alkenyl. Q⁴ is such as OCH═CH₂, OCH₂CH═CH₂.

According to a further specific embodiment of formula I, Q⁴ is ORwherein R C₂-C₆-alkynyl, in particular C₂-C₆-alkynyl, in particularC₂-C₄-alkynyl, more specifically C₁-C₂-alkynyl. Q⁴ is such as OC≡CH

According to still another embodiment of formula I, Q⁴ is OR^(Y),wherein R is C₃-C₆-halogencycloalkyl. In a special embodiment R¹ isfully or partially halogenated cyclopropyl.

According to still another embodiment of formula I, Q⁴ is OR^(Y) whereinR^(Y) and phenyl; wherein the phenyl groups are unsubstituted or carryone, two, three, four or five substituents selected from the groupconsisting of CN, halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy.

According to still another embodiment of formula I, Q⁴ is OR wherein Rphenyl-C₁-C₆-alkyl, such as phenyl-CH₂, herein the phenyl groups areunsubstituted or carry one, two, three, four or five substituentsselected from the group consisting of CN, halogen, OH, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy. Q⁴ is such asOCH₂Ph.

According to still a further embodiment of formula I, Q⁴ isC₂-C₆-alkenyl, in particular C₂-C₄-alkenyl, such as CH═CH₂, C(CH₃)═CH₂,CH₂CH═CH₂.

According to a further specific embodiment of formula I, Q⁴ isC₂-C₆-halogenalkenyl, in particular C₂-C₄-halogenalkenyl, morespecifically C₂-C₃-halogenalkenyl such as CH═CHF, CH═CHCl, CH═CF₂,CH═CCl₂, CH₂CH═CHF, CH₂CH═CHCl, CH₂CH═CF₂, CH₂CH═CCl₂, CF₂CH═CF₂,CCl₂CH═CCl₂, CF₂CF═CF₂, CCl₂CCl═CCl₂.

According to still a further embodiment of formula I, Q⁴ isC₂-C₆-alkynyl or C₂-C₆-halogenalkynyl, in particular C₂-C₄-alkynyl orC₂-C₄-halogenalkynyl, such as C≡CH, CH₂C≡CH.

According to still another embodiment of formula I, Q⁴ isS(O)n-C₁-C₆-alkyl such as SCH₃, S(═O) CH₃, S(O)₂CH₃.

According to still another embodiment of formula I, Q⁴ isS(O)n-C₁-C₆-halogenalkyl such as SCF₃, S(═O)CF₃, S(O)₂CF₃, SCHF₂,S(═O)CHF₂, S(O)₂CHF₂.

According to still another embodiment of formula I, Q⁴ is S(O)n-arylsuch as S-phenyl, S(═O) phenyl, S(O)₂phenyl, wherein the phenyl group isunsubstituted or carries one, two, three, four or five substituentsR^(78a) selected from the group consisting of halogen, OH, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;

According to still another embodiment of formula I, Q⁴ isS(O)n-C₂-C₆-alkenyl such as SCH═CH₂, S(═O)CH═CH₂, S(O)₂CH═CH₂,SCH₂CH═CH₂, S(═O)CH₂CH═CH₂, S(O)₂CH₂CH═CH₂.

According to still another embodiment of formula I, Q⁴ isS(O)n-C₂-C₆-alkynyl such as SC≡CH, S(═O)C≡CH, S(O)₂C≡CH, SCH₂C≡CH,S(═O)CH₂C≡CH, S(O)₂CH₂C≡CH.

According to still another embodiment of formula I, Q⁴ isSO₂—NH(C₁-C₆-alkyl), is C₁-C₆-alkyl, in particular C₁-C₄-alkyl, morespecifically C₁-C₂-alkyl. Q⁴ is such as SO₂NHCH₃ or SO₂NHCH₂CH₃.

According to still another embodiment of formula I, Q⁴ isSO₂—NH(C₁-C₆-halogenalkyl), wherein C₁-C₆-halogenalkyl, in particularC₁-C₄-halogenalkyl, more specifically C₁-C₂-halogenalkyl. Q⁴ is such asSO₂NHCF₃, SO₂NHCHF₂, SO₂NHCH₂F, SO₂NHCCl₃, SO₂NHCHCl₂ or SO₂NHCH₂Cl, inparticular SO₂NHCF₃, SO₂NHCHF₂, SO₂NHCCl₃ or SO₂NHCHCl₂.

According to still another embodiment of formula I, Q⁴ is SO₂—NHaryl,wherein the aryl groups are unsubstituted or carry one, two, three, fouror five substituents selected from the group consisting of CN, halogen,OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy. Q⁴ is such as SO₂NHPh.

According to still another embodiment of formula I, Q⁴ is tri-(C₁-C₆alkyl)silyl, in particular C₁-C₄-alkyl, such as CH₃. or C₂H₅. Q⁴ is suchas OSi(CH₃)₃

According to still another embodiment of formula I, Q⁴ is di-(C₁-C₆alkoxy)phosphoryl), in particular C₁-C₄-alkoxy, such as OCH₃. orOC₂H₅.Q⁴ is such as OPO(OCH₃)₂.

According to still another embodiment of formula I, Q⁴ isphenyl-C₁-C₆-alkyl, such as phenyl-CH₂, wherein the phenyl moiety ineach case is unsubstituted or substituted by one, two or three identicalor different groups Q^(4b) which independently of one another areselected from halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl andC₁-C₂-halogenalkoxy, in particular F, C, Br, CH₃, OCH₃, CF₃ and OCF₃.

According to still another embodiment of formula I, Q⁴ is aryl, inparticular phenyl, wherein the aryl or phenyl moiety in each case isunsubstituted or substituted by identical or different groups Q^(4b)which independently of one another are selected from halogen,C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-halogenalkyl and C₁-C₂-halogenalkoxy,in particular F, C, Br, CH₃, OCH₃, CF₃ and OCF₃. According to oneembodiment, Q⁴ is unsubstituted phenyl. According to another embodiment,Q⁴ is phenyl, that is substituted by one, two or three, in particularone, halogen, in particular selected from F, Cl and Br, morespecifically selected from F and Cl.

According to still another embodiment of formula I, Q⁴ is a 5-memberedheteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl,thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl,pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl,imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl,isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl,1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.

According to still another embodiment of formula I, Q⁴ is a 6-memberedheteroaryl such as pyri-din-2-yl, pyridin-3-yl, pyridin-4-yl,pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and1,2,4-triazin-3-yl.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H, halogen, OH, CN, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₁-C₆-halogenalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy andC₃-C₆-cycloalkyl wherein the acyclic moieties of Q⁴ are unsubstituted orsubstituted with identical or different groups Q⁴ as defined andpreferably defined herein, and wherein the carbocyclic, phenyl andheteroaryl moieties of Q⁴ are unsubstituted or substituted withidentical or different groups Q^(4b) as defined and preferably definedherein.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H, halogen, OH, CN, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy,C₃-C₆-alkynyloxy and C₃-C₆-cycloalkyl, wherein the acyclic moieties ofQ⁴ are unsubstituted or substituted with identical or different groupsQ⁴ as defined and preferably defined herein, and wherein the cycloalkylmoieties of Q⁴ are unsubstituted or substituted with identical ordifferent groups Q^(4b) as defined and preferably defined herein.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H and OR^(Y), wherein R is most preferablyC₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-halogenalkenyl,C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl, phenyl and phenyl-C₁-C₆-alkyl;wherein the phenyl groups are unsubstituted or carry one, two, three,four or five substituents selected from the group consisting of CN,halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H and OR^(Y), wherein R is most preferablyC₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl and phenyl-C₁-C₆-alkyl; wherein thephenyl groups are unsubstituted or carry one, two, three, four or fivesubstituents selected from the group consisting of CN, halogen,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H, CH(═O), C(═O)C₁-C₆-alkyl,C(═O)O(C₁-C₆-alkyl) and C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl),C(═O)C₂-C₆-alkenyl, C(═O)O(C₂-C₆-alkenyl), C(═O)NH(C₂-C₆-alkenyl),C(═O)N(C₂-C₆-alkenyl), C(═O)C₂-C₆-alkynyl, C(═O)O(C₂-C₆-alkynyl),C(═O)NH(C₂-C₆-alkynyl), C(═O)N(C₂-C₆-alkynyl)₂C(═O)C₃-C₆-cycloalkyl,C(═O)O(C₃-C₆-cycloalkyl), C(═O)NH(C₃-C₆-cycloalkyl) andC(═O)N(C₃-C₆-cycloalkyl)₂, wherein the acyclic moieties of Q⁴ areunsubstituted or substituted with identical or different groups Q⁴ asdefined and preferably defined herein, and wherein the cycloalkylmoieties of Q⁴ are unsubstituted or substituted with identical ordifferent groups Q^(4b) as defined and preferably defined herein.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H, C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl),C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl), C(═O)C₂-C₆-alkenyl,C(═O)O(C₂-C₆-alkenyl), C(═O)NH(C₂-C₆-alkenyl), C(═O)N(C₂-C₆-alkenyl),wherein the acyclic moieties of Q⁴ are unsubstituted or substituted withidentical or different groups Q⁴ as defined and preferably definedherein, and wherein the cycloalkyl moieties of Q⁴ are unsubstituted orsubstituted with identical or different groups Q^(4b) as defined andpreferably defined herein.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H, S(O)n-C₁-C₆-alkyl,S(O)_(n)—C₁-C₆-halogenalkyl, S(O), —C₁-C₆-alkoxy,S(O)_(n)—C₂-C₆-alkenyl, S(O)_(n)—C₂-C₆-alkynyl, S(O)_(n)aryl, whereinthe acyclic moieties of Q⁴ are unsubstituted or substituted withidentical or different groups Q⁴ as defined and preferably definedherein, and wherein the aryl moieties of Q⁴ are unsubstituted orsubstituted with identical or different groups Q^(4b) as defined andpreferably defined herein.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H, SO₂—NH(C₁-C₆-alkyl),SO₂—NH(C₁-C₆-halogenalkyl), SO₂—NHphenyl, wherein the acyclic moietiesof Q⁴ are unsubstituted or substituted with identical or differentgroups Q⁴ as defined and preferably defined herein, and wherein the arylmoieties of Q⁴ are unsubstituted or substituted with identical ordifferent groups Q^(4b) as defined and preferably defined herein.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H, C₁-C₆-alkyl, C(═O)C₁-C₆-alkyl,C(═O)O(C₁-C₆-alkyl), S(O)n-C₁-C₆-alkyl, S(O)_(n)aryl, wherein theacyclic moieties of Q⁴ are unsubstituted or substituted with identicalor different groups Q⁴ as defined and preferably defined herein, andwherein the aryl moieties of Q⁴ are unsubstituted or substituted withidentical or different groups Q^(4b) as defined and preferably definedherein.

According to still another embodiment of formula I, Q⁴ is in each caseindependently selected from H, C(═O)C₁-C₆-alkyl, C(═O)OC₁-C₆-alkyl,C(═O)NHC₁-C₆-alkyl, S(O)₂—C₁-C₆-alkyl, S(O)₂-aryl, SO₂—NH(C₁-C₆-alkyl),OR^(Y), or C₁-C₄-alkyl; wherein R^(Y) is C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl.

According to one embodiment Q^(4a) is independently selected fromhalogen, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl andC₁-C₄-halogenalkoxy. Specifically, Q⁴ is independently selected from F,C, Br, I, C₁-C₂-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1-Cl-cyclopropyl,1,1-F₂-cyclopropyl, 1,1-Cl₂-cyclopropyl and C₁-C₂-halogenalkoxy.

According to still another embodiment of formula I, Q⁴ is independentlyhalogen, in particular selected from F, Cl, Br and I, more specificallyF, Cl and Br.

Q⁴ are the possible substituents for the cycloalkyl, heteroaryl andphenyl moieties of Q⁴. Q⁴ according to the invention is independentlyselected from halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio.

According to one embodiment thereof Q⁴ is independently selected fromhalogen, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl andC₁-C₄-halogenalkoxy, in particular halogen, C₁-C₄-alkyl andC₁-C₄-alkoxy. Specifically, Q⁴ is independently selected from F, Cl, CN,CH₃, CHF₂, CF₃OCH₃ and halogenmethoxy.

Particularly preferred embodiments of Q⁴ according to the invention arein Table Q4 below, wherein each line of lines Q⁴-1 to Q⁴-50 correspondsto one particular embodiment of the invention, wherein Q⁴-1 to Q⁴-50 arealso in any combination with one another a preferred embodiment of thepresent invention. The connection point to the carbon atom, to which Q⁴is bound is marked with “#” in the drawings.

TABLE Q4 No. Q⁴ P12-1 H P12-2 CH₃ P12-3 CH₂F P12-4 CHF₂ P12-5 CF₃ P12-6C₂H₅ P12-7 C₃H₇ P12-8 CH(CH₃)₂ P12-9 CH₂CH₂CH₃ P12-10 CH₂CH₂CH₂CH₃P12-11 CH₂CH(CH₃)₂ P12-12 C(CH₃)₃ P12-13 CH₂CH₂CH₂CH₂CH₃ P12-14 CH═CH₂P12-15 CH₂CH═CH₂ P12-16 C≡CH P12-17 CH₂C≡CH P12-18 CH₂CH₂CH(CH₃)₂ P12-19OH P12-20 OCH₃ P12-21 OCHF₂ P12-22 OC₂H₅ P12-23 OCH₂OCH₃ P12-24 OCH₂PhP12-25 OCH₂CH═CH₂ P12-26 C(O)CH₃ P12-27 C(O)OCH₃ P12-28 C(O)OCH₂CH₃P12-29 C(O)OCH(CH₃)₂ P12-30 C(O)OC(CH₃)₃ P12-31 CO—NH₂ P12-32 CO—NH(CH₃)P12-33 CO—N(CH₃)₂ P12-34 SO₂H P12-35 SO₂—CH₃ P12-36 SO—CH₃ P12-37 S—CH₃P12-38 SO₂NHCH₃ P12-39 SO₂NHCF₃ P12-40 SO₂NHPh P12-41 SO₂Ph P12-42SO₂C₆H₄-4-CH₃ P12-43 Si(CH₃)₃ P12-44 PO(OCH₃)₂ P12-45

P12-46

P12-47

P12-48

P12-49

P12-50

Particular embodiments of the compounds I are the following compounds:I-A, I-B, I-C, I-D, I-E, I-F; II-A, II-B, II-C, II-D, II-E, II-F. Inthese formulae, the substituents Q¹, Q² and Q³ are independently asdefined in claim 1 or preferably defined below:

Table 1-1 Compounds of the formula I-A, I-B, I-C, I-D, I-E, I-F in whichthe meaning for the combination of Q¹, Q² and Q³ for each individualcompound corresponds in each case to one line of Table A (compoundsI-A.1-1.A-1 to I-A.1-1.A-874, I-B.1-1.A-1 to I-B.1-1.A-874, I-C.1-1.A-1to I-C.1-1.A-874, I-D.1-1.A-1 to I-D.1-1.A-874, I-E.1-1.A-1 toI-E.1-1.A-874, I-F.1-1.A-1 to I-F.1-1.A-874).

Table 2-1 Compounds of the formula II-A, II-B, II-C, II-D, II-E, II-F inwhich the meaning for the combination of Q¹, Q² and Q³ for eachindividual compound corresponds in each case to one line of Table A(compounds II-A.2-1.A-1 to II-A.2-1.A-874, II-B.2-1.A-1 toII-B.2-1.A-874, II-C.2-1.A-1 to II-C.2-1.A-874, II-D.2-1.A-1 toII-D.2-1.A-874, II-E.2-1.A-1 to II-E.2-1.A-874, II-F.2-1.A-1 toII-F.2-1.A-874).

TABLE A No. Q³ Q¹ Q² A-1 COCH₃ F F A-2 COCH₂CH₃ F F A-3 COCH₂CH₂CH₃ F FA-4 CO(CH₂)₃CH₃ F F A-5 CO(CH₂)₄CH₃ F F A-6 CO(CH₂)₅CH₃ F F A-7CO(CH₂)₆CH₃ F F A-8 COCCl₃ F F A-9 COCH₂Cl F F A-10 COCH₂-N(CH₃)₂ F FA-11 COPh F F A-12 COCH₂Ph F F A-13 COCH₂Ph-4-F F F A-14 COCH₂Ph-4-CH₃ FF A-15 COCH₂Ph-3-CH₃ F F A-16 COCH₂Ph-2-CH₃ F F A-17 COCH(CH₃)Ph F FA-18 COCH(CH₃)-4-F F F A-19 COCH(CH₃)-4-CH₃ F F A-20 COCH(CH₃)-3-CH₃ F FA-21 COCH(CH₃)-3-CH₃ F F A-22 CF₃ F F A-23 CHF₂ F F A-24 CH₂CH₂OCH₃ F FA-25 CH₂cPr F F A-26 C₆H₅ F F A-27 CH₂—C₆H₅ F F A-28 CH₂—C₆H₄-4-F F FA-29 CH₂—C₆H₄-4-CH₃ F F A-30 CH₂—C₆H₄-3-CH₃ F F A-31 CH₂—C₆H₄-2-CH₃ F FA-32 CH(CH₃)—C₆H₅ F F A-33 CH(CH₃)—C₆H₄-4-F F F A-34 CH(CH₃)—C₆H₄-4-CH₃F F A-35 CH(CH₃)—C₆H₄-3-CH₃ F F A-36 CH(CH₃)—C₆H₄-2-CH₃ F F A-37

F F A-38

F F A-39

F F A-40 2-py F F A-41 3-py F F A-42

F F A-43

F F A-44

F F A-45

F F A-46

F F A-47 COCH₃ CF₃ CF₃ A-48 COCH₂CH₃ CF₃ CF₃ A-49 COCH₂CH₂CH₃ CF₃ CF₃A-50 CO(CH₂)₃CH₃ CF₃ CF₃ A-51 CO(CH₂)₄CH₃ CF₃ CF₃ A-52 CO(CH₂)₅CH₃ CF₃CF₃ A-53 CO(CH₂)₆CH₃ CF₃ CF₃ A-54 COCCl₃ CF₃ CF₃ A-55 COCH₂Cl CF₃ CF₃A-56 COCH₂—N(CH₃)₂ CF₃ CF₃ A-57 COPh CF₃ CF₃ A-58 COCH₂Ph CF₃ CF₃ A-59COCH₂Ph-4-F CF₃ CF₃ A-60 COCH₂Ph-4-CH₃ CF₃ CF₃ A-61 COCH₂Ph-3-CH₃ CF₃CF₃ A-62 COCH₂Ph-2-CH₃ CF₃ CF₃ A-63 COCH(CH₃)Ph CF₃ CF₃ A-64COCH(CH₃)-4-F CF₃ CF₃ A-65 COCH(CH₃)-4-CH₃ CF₃ CF₃ A-66 COCH(CH₃)-3-CH₃CF₃ CF₃ A-67 COCH(CH₃)-3-CH₃ CF₃ CF₃ A-68 CF₃ CF₃ CF₃ A-69 CHF₂ CF₃ CF₃A-70 CH₂CH₂OCH₃ CF₃ CF₃ A-71 CH₂cPr CF₃ CF₃ A-72 C₆H₅ CF₃ CF₃ A-73CH₂—C₆H₅ CF₃ CF₃ A-74 CH₂—C₆H₄-4-F CF₃ CF₃ A-75 CH₂—C₆H₄-4-CH₃ CF₃ CF₃A-76 CH₂—C₆H₄-3-CH₃ CF₃ CF₃ A-77 CH₂—C₆H₄-2-CH₃ CF₃ CF₃ A-78CH(CH₃)—C₆H₅ CF₃ CF₃ A-79 CH(CH₃)—C₆H₄-4-F CF₃ CF₃ A-80CH(CH₃)—C₆H₄-4-CH₃ CF₃ CF₃ A-81 CH(CH₃)—C₆H₄-3-CH₃ CF₃ CF₃ A-82CH(CH₃)—C₆H₄-2-CH₃ CF₃ CF₃ A-83

CF₃ CF₃ A-84

CF₃ CF₃ A-85

CF₃ CF₃ A-86 2-py CF₃ CF₃ A-87 3-Py CF₃ CF₃ A-88

CF₃ CF₃ A-89

CF₃ CF₃ A-90

CF₃ CF₃ A-91

CF₃ CF₃ A-92

CF₃ CF₃ A-93 COCH₃ C₃H₇ (cyclopropyl) H A-94 COCH₂CH₃ C₃H₇ (cyclopropyl)H A-95 COCH₂CH₂CH₃ C₃H₇ (cyclopropyl) H A-96 CO(CH₂)₃CH₃ C₃H₇(cyclopropyl) H A-97 CO(CH₂)₄CH₃ C₃H₇ (cyclopropyl) H A-98 CO(CH₂)₅CH₃C₃H₇ (cyclopropyl) H A-99 CO(CH₂)₆CH₃ C₃H₇ (cyclopropyl) H A-100 COCCl₃C₃H₇ (cyclopropyl) H A-101 COCH₂Cl C₃H₇ (cyclopropyl) H A-102COCH₂—N(CH₃)₂ C₃H₇ (cyclopropyl) H A-103 COPh C₃H₇ (cyclopropyl) H A-104COCH₂Ph C₃H₇ (cyclopropyl) H A-105 COCH₂Ph-4-F C₃H₇ (cyclopropyl) HA-106 COCH₂Ph-4-CH₃ C₃H₇ (cyclopropyl) H A-107 COCH₂Ph-3-CH₃ C₃H₇(cyclopropyl) H A-108 COCH₂Ph-2-CH₃ C₃H₇ (cyclopropyl) H A-109COCH(CH₃)Ph C₃H₇ (cyclopropyl) H A-110 COCH(CH₃)-4-F C₃H₇ (cyclopropyl)H A-111 COCH(CH₃)-4-CH₃ C₃H₇ (cyclopropyl) H A-112 COCH(CH₃)-3-CH₃ C₃H₇(cyclopropyl) H A-113 COCH(CH₃)-3-CH₃ C₃H₇ (cyclopropyl) H A-114 CF₃C₃H₇ (cyclopropyl) H A-115 CHF₂ C₃H₇ (cyclopropyl) H A-116 CH₂CH₂OCH₃C₃H₇ (cyclopropyl) H A-117 CH₂cPr C₃H₇ (cyclopropyl) H A-118 C₆H₅ C₃H₇(cyclopropyl) H A-119 CH₂—C₆H₅ C₃H₇ (cyclopropyl) H A-120 CH₂—C₆H₄-4-FC₃H₇ (cyclopropyl) H A-121 CH₂—C₆H₄-4-CH₃ C₃H₇ (cyclopropyl) H A-122CH₂—C₆H₄-3-CH₃ C₃H₇ (cyclopropyl) H A-123 CH₂—C₆H₄-2-CH₃ C₃H₇(cyclopropyl) H A-124 CH(CH₃)—C₆H₅ C₃H₇ (cyclopropyl) H A-125CH(CH₃)—C₆H₄-4-F C₃H₇ (cyclopropyl) H A-126 CH(CH₃)—C₆H₄-4-CH₃ C₃H₇(cyclopropyl) H A-127 CH(CH₃)—C₆H₄-3-CH₃ C₃H₇ (cyclopropyl) H A-128CH(CH₃)—C₆H₄-2-CH₃ C₃H₇ (cyclopropyl) H A-129

C₃H₇ (cyclopropyl) H A-130

C₃H₇ (cyclopropyl) H A-131

C₃H₇ (cyclopropyl) H A-132 2-py C₃H₇ (cyclopropyl) H A-133 3-Py C₃H₇(cyclopropyl) H A-134

C₃H₇ (cyclopropyl) H A-135

C₃H₇ (cyclopropyl) H A-136

C₃H₇ (cyclopropyl) H A-137

C₃H₇ (cyclopropyl) H A-138

C₃H₇ (cyclopropyl) H A-139 COCH₃ i-C₃H₇ H A-140 COCH₂CH₃ i-C₃H₇ H A-141COCH₂CH₂CH₃ i-C₃H₇ H A-142 CO(CH₂)₃CH₃ i-C₃H₇ H A-143 CO(CH₂)₄CH₃ i-C₃H₇H A-144 CO(CH₂)₅CH₃ i-C₃H₇ H A-145 CO(CH₂)₆CH₃ i-C₃H₇ H A-146 COCCl₃i-C₃H₇ H A-147 COCH₂Cl i-C₃H₇ H A-148 COCH₂—N(CH₃)₂ i-C₃H₇ H A-149 COPhi-C₃H₇ H A-150 COCH₂Ph i-C₃H₇ H A-151 COCH₂Ph-4-F i-C₃H₇ H A-152COCH₂Ph-4-CH₃ i-C₃H₇ H A-153 COCH₂Ph-3-CH₃ i-C₃H₇ H A-154 COCH₂Ph-2-CH₃i-C₃H₇ H A-155 COCH(CH₃)Ph i-C₃H₇ H A-156 COCH(CH₃)-4-F i-C₃H₇ H A-157COCH(CH₃)-4-CH₃ i-C₃H₇ H A-158 COCH(CH₃)-3-CH₃ i-C₃H₇ H A-159COCH(CH₃)-3-CH₃ i-C₃H₇ H A-160 CF₃ i-C₃H₇ H A-161 CHF₂ i-C₃H₇ H A-162CH₂CH₂OCH₃ i-C₃H₇ H A-163 CH₂cPr i-C₃H₇ H A-164 C₆H₅ i-C₃H₇ H A-165CH₂—C₆H₅ i-C₃H₇ H A-166 CH₂—C₆H₄-4-F i-C₃H₇ H A-167 CH₂—C₆H₄-4-CH₃i-C₃H₇ H A-168 CH₂—C₆H₄-3-CH₃ i-C₃H₇ H A-169 CH₂—C₆H₄-2-CH₃ i-C₃H₇ HA-170 CH(CH₃)—C₆H₅ i-C₃H₇ H A-171 CH(CH₃)—C₆H₄-4-F i-C₃H₇ H A-172CH(CH₃)—C₆H₄-4-CH₃ i-C₃H₇ H A-173 CH(CH₃)—C₆H₄-3-CH₃ i-C₃H₇ H A-174CH(CH₃)—C₆H₄-2-CH₃ i-C₃H₇ H A-175

i-C₃H₇ H A-176

i-C₃H₇ H A-177

i-C₃H₇ H A-178 2-py i-C₃H₇ H A-179 3-Py i-C₃H₇ H A-180

i-C₃H₇ H A-181

i-C₃H₇ H A-182

i-C₃H₇ H A-183

i-C₃H₇ H A-184

i-C₃H₇ H A-185 COCH₃ CCH H A-186 COCH₂CH₃ CCH H A-187 COCH₂CH₂CH₃ CCH HA-188 CO(CH₂)₃CH₃ CCH H A-189 CO(CH₂)₄CH₃ CCH H A-190 CO(CH₂)₅CH₃ CCH HA-191 CO(CH₂)₆CH₃ CCH H A-192 COCCl₃ CCH H A-193 COCH₂Cl CCH H A-194COCH₂—N(CH₃)₂ CCH H A-195 COPh CCH H A-196 COCH₂Ph CCH H A-197COCH₂Ph-4-F CCH H A-198 COCH₂Ph-4-CH₃ CCH H A-199 COCH₂Ph-3-CH₃ CCH HA-200 COCH₂Ph-2-CH₃ CCH H A-201 COCH(CH₃)Ph CCH H A-202 COCH(CH₃)-4-FCCH H A-203 COCH(CH₃)-4-CH₃ CCH H A-204 COCH(CH₃)-3-CH₃ CCH H A-205COCH(CH₃)-3-CH₃ CCH H A-206 CF₃ CCH H A-207 CHF₂ CCH H A-208 CH₂CH₂OCH₃CCH H A-209 CH₂cPr CCH H A-210 C₆H₅ CCH H A-211 CH₂—C₆H₅ CCH H A-212CH₂—C₆H₄-4-F CCH H A-213 CH₂—C₆H₄-4-CH₃ CCH H A-214 CH₂—C₆H₄-3-CH₃ CCH HA-215 CH₂—C₆H₄-2-CH₃ CCH H A-216 CH(CH₃)—C₆H₅ CCH H A-217CH(CH₃)—C₆H₄-4-F CCH H A-218 CH(CH₃)—C₆H₄-4-CH₃ CCH H A-219CH(CH₃)—C₆H₄-3-CH₃ CCH H A-220 CH(CH₃)—C₆H₄-2-CH₃ CCH H A-221

CCH H A-222

CCH H A-223

CCH H A-224 2-py CCH H A-225 3-Py CCH H A-226

CCH H A-227

CCH H A-228

CCH H A-229

CCH H A-230

CCH H A-231 COCH₃ CH═CH₂ H A-232 COCH₂CH₃ CH═CH₂ H A-233 COCH₂CH₂CH₃CH═CH₂ H A-234 CO(CH₂)₃CH₃ CH═CH₂ H A-235 CO(CH₂)₄CH₃ CH═CH₂ H A-236CO(CH₂)₅CH₃ CH═CH₂ H A-237 CO(CH₂)₆CH₃ CH═CH₂ H A-238 COCCl₃ CH═CH₂ HA-239 COCH₂Cl CH═CH₂ H A-240 COCH₂—N(CH₃)₂ CH═CH₂ H A-241 COPh CH═CH₂ HA-242 COCH₂Ph CH═CH₂ H A-243 COCH₂Ph-4-F CH═CH₂ H A-244 COCH₂Ph-4-CH₃CH═CH₂ H A-245 COCH₂Ph-3-CH₃ CH═CH₂ H A-246 COCH₂Ph-2-CH₃ CH═CH₂ H A-247COCH(CH₃)Ph CH═CH₂ H A-248 COCH(CH₃)-4-F CH═CH₂ H A-249 COCH(CH₃)-4-CH₃CH═CH₂ H A-250 COCH(CH₃)-3-CH₃ CH═CH₂ H A-251 COCH(CH₃)-3-CH₃ CH═CH₂ HA-252 CF₃ CH═CH₂ H A-253 CHF₂ CH═CH₂ H A-254 CH₂CH₂OCH₃ CH═CH₂ H A-255CH₂cPr CH═CH₂ H A-256 C₆H₅ CH═CH₂ H A-257 CH₂—C₆H₅ CH═CH₂ H A-258CH₂—C₆H₄-4-F CH═CH₂ H A-259 CH₂—C₆H₄-4-CH₃ CH═CH₂ H A-260 CH₂—C₆H₄-3-CH₃CH═CH₂ H A-261 CH₂—C₆H₄-2-CH₃ CH═CH₂ H A-262 CH(CH₃)—C₆H₅ CH═CH₂ H A-263CH(CH₃)—C₆H₄-4-F CH═CH₂ H A-264 CH(CH₃)—C₆H₄-4-CH₃ CH═CH₂ H A-265CH(CH₃)—C₆H₄-3-CH₃ CH═CH₂ H A-266 CH(CH₃)—C₆H₄-2-CH₃ CH═CH₂ H A-267

CH═CH₂ H A-268

CH═CH₂ H A-269

CH═CH₂ H A-270 2-py CH═CH₂ H A-271 3-Py CH═CH₂ H A-272

CH═CH₂ H A-273

CH═CH₂ H A-274

CH═CH₂ H A-275

CH═CH₂ H A-276

CH═CH₂ H A-277 COCH₃ CH₂CH═CH₂ H A-278 COCH₂CH₃ CH₂CH═CH₂ H A-279COCH₂CH₂CH₃ CH₂CH═CH₂ H A-280 CO(CH₂)₃CH₃ CH₂CH═CH₂ H A-281 CO(CH₂)₄CH₃CH₂CH═CH₂ H A-282 CO(CH₂)₅CH₃ CH₂CH═CH₂ H A-283 CO(CH₂)₆CH₃ CH₂CH═CH₂ HA-284 COCCl₃ CH₂CH═CH₂ H A-285 COCH₂Cl CH₂CH═CH₂ H A-286 COCH₂—N(CH₃)₂CH₂CH═CH₂ H A-287 COPh CH₂CH═CH₂ H A-288 COCH₂Ph CH₂CH═CH₂ H A-289COCH₂Ph-4-F CH₂CH═CH₂ H A-290 COCH₂Ph-4-CH₃ CH₂CH═CH₂ H A-291COCH₂Ph-3-CH₃ CH₂CH═CH₂ H A-292 COCH₂Ph-2-CH₃ CH₂CH═CH₂ H A-293COCH(CH₃)Ph CH₂CH═CH₂ H A-294 COCH(CH₃)-4-F CH₂CH═CH₂ H A-295COCH(CH₃)-4-CH₃ CH₂CH═CH₂ H A-296 COCH(CH₃)-3-CH₃ CH₂CH═CH₂ H A-297COCH(CH₃)-3-CH₃ CH₂CH═CH₂ H A-298 CF₃ CH₂CH═CH₂ H A-299 CHF₂ CH₂CH═CH₂ HA-300 CH₂CH₂OCH₃ CH₂CH═CH₂ H A-301 CH₂cPr CH₂CH═CH₂ H A-302 C₆H₅CH₂CH═CH₂ H A-303 CH₂—C₆H₅ CH₂CH═CH₂ H A-304 CH₂—C₆H₄-4-F CH₂CH═CH₂ HA-305 CH₂—C₆H₄-4-CH₃ CH₂CH═CH₂ H A-306 CH₂—C₆H₄-3-CH₃ CH₂CH═CH₂ H A-307CH₂—C₆H₄-2-CH₃ CH₂CH═CH₂ H A-308 CH(CH₃)—C₆H₅ CH₂CH═CH₂ H A-309CH(CH₃)—C₆H₄-4-F CH₂CH═CH₂ H A-310 CH(CH₃)—C₆H₄-4-CH₃ CH₂CH═CH₂ H A-311CH(CH₃)—C₆H₄-3-CH₃ CH₂CH═CH₂ H A-312 CH(CH₃)—C₆H₄-2-CH₃ CH₂CH═CH₂ HA-313

CH₂CH═CH₂ H A-314

CH₂CH═CH₂ H A-315

CH₂CH═CH₂ H A-316 2-py CH₂CH═CH₂ H A-317 3-Py CH₂CH═CH₂ H A-318

CH₂CH═CH₂ H A-319

CH₂CH═CH₂ H A-320

CH₂CH═CH₂ H A-321

CH₂CH═CH₂ H A-322

CH₂CH═CH₂ H A-323 COCH₃ CN H A-324 COCH₂CH₃ CN H A-325 COCH₂CH₂CH₃ CN HA-326 CO(CH₂)₃CH₃ CN H A-327 CO(CH₂)₄CH₃ CN H A-328 CO(CH₂)₅CH₃ CN HA-329 CO(CH₂)₆CH₃ CN H A-330 COCCl₃ CN H A-331 COCH₂Cl CN H A-332COCH₂—N(CH₃)₂ CN H A-333 COPh CN H A-334 COCH₂Ph CN H A-335 COCH₂Ph-4-FCN H A-336 COCH₂Ph-4-CH₃ CN H A-337 COCH₂Ph-3-CH₃ CN H A-338COCH₂Ph-2-CH₃ CN H A-339 COCH(CH₃)Ph CN H A-340 COCH(CH₃)-4-F CN H A-341COCH(CH₃)-4-CH₃ CN H A-342 COCH(CH₃)-3-CH₃ CN H A-343 COCH(CH₃)-3-CH₃ CNH A-344 CF₃ CN H A-345 CHF₂ CN H A-346 CH₂CH₂OCH₃ CN H A-347 CH₂cPr CN HA-348 C₆H₅ CN H A-349 CH₂—C₆H₅ CN H A-350 CH₂—C₆H₄-4-F CN H A-351CH₂—C₆H₄-4-CH₃ CN H A-352 CH₂—C₆H₄-3-CH₃ CN H A-353 CH₂—C₆H₄-2-CH₃ CN HA-354 CH(CH₃)—C₆H₅ CN H A-355 CH(CH₃)—C₆H₄-4-F CN H A-356CH(CH₃)—C₆H₄-4-CH₃ CN H A-357 CH(CH₃)—C₆H₄-3-CH₃ CN H A-358CH(CH₃)—C₆H₄-2-CH₃ CN H A-359

CN H A-360

CN H A-361

CN H A-362 2-py CN H A-363 3-Py CN H A-364

CN H A-365

CN H A-366

CN H A-367

CN H A-368

CN H A-369 COCH₃ C₆H₅ H A-370 COCH₂CH₃ C₆H₅ H A-371 COCH₂CH₂CH₃ C₆H₅ HA-372 CO(CH₂)₃CH₃ C₆H₅ H A-373 CO(CH₂)₄CH₃ C₆H₅ H A-374 CO(CH₂)₅CH₃ C₆H₅H A-375 CO(CH₂)₆CH₃ C₆H₅ H A-376 COCCl₃ C₆H₅ H A-377 COCH₂Cl C₆H₅ HA-378 COCH₂—N(CH₃)₂ C₆H₅ H A-379 COPh C₆H₅ H A-380 COCH₂Ph C₆H₅ H A-381COCH₂Ph-4-F C₆H₅ H A-382 COCH₂Ph-4-CH₃ C₆H₅ H A-383 COCH₂Ph-3-CH₃ C₆H₅ HA-384 COCH₂Ph-2-CH₃ C₆H₅ H A-385 COCH(CH₃)Ph C₆H₅ H A-386 COCH(CH₃)-4-FC₆H₅ H A-387 COCH(CH₃)-4-CH₃ C₆H₅ H A-388 COCH(CH₃)-3-CH₃ C₆H₅ H A-389COCH(CH₃)-3-CH₃ C₆H₅ H A-390 CF₃ C₆H₅ H A-391 CHF₂ C₆H₅ H A-392CH₂CH₂OCH₃ C₆H₅ H A-393 CH₂cPr C₆H₅ H A-394 C₆H₅ C₆H₅ H A-395 CH₂—C₆H₅C₆H₅ H A-396 CH₂—C₆H₄-4-F C₆H₅ H A-397 CH₂—C₆H₄-4-CH₃ C₆H₅ H A-398CH₂—C₆H₄-3-CH₃ C₆H₅ H A-399 CH₂—C₆H₄-2-CH₃ C₆H₅ H A-400 CH(CH₃)—C₆H₅C₆H₅ H A-401 CH(CH₃)—C₆H₄-4-F C₆H₅ H A-402 CH(CH₃)—C₆H₄-4-CH₃ C₆H₅ HA-403 CH(CH₃)—C₆H₄-3-CH₃ C₆H₅ H A-404 CH(CH₃)—C₆H₄-2-CH₃ C₆H₅ H A-405

C₆H₅ H A-406

C₆H₅ H A-407

C₆H₅ H A-408 2-py C₆H₅ H A-409 3-Py C₆H₅ H A-410

C₆H₅ H A-411

C₆H₅ H A-412

C₆H₅ H A-413

C₆H₅ H A-414

C₆H₅ H A-415 COCH₃ CH₂—C₆H₅ H A-416 COCH₂CH₃ CH₂—C₆H₅ H A-417COCH₂CH₂CH₃ CH₂—C₆H₅ H A-418 CO(CH₂)₃CH₃ CH₂—C₆H₅ H A-419 CO(CH₂)₄CH₃CH₂—C₆H₅ H A-420 CO(CH₂)₅CH₃ CH₂—C₆H₅ H A-421 CO(CH₂)₆CH₃ CH₂—C₆H₅ HA-422 COCCl₃ CH₂—C₆H₅ H A-423 COCH₂Cl CH₂—C₆H₅ H A-424 COCH₂—N(CH₃)₂CH₂—C₆H₅ H A-425 COPh CH₂—C₆H₅ H A-426 COCH₂Ph CH₂—C₆H₅ H A-427COCH₂Ph-4-F CH₂—C₆H₅ H A-428 COCH₂Ph-4-CH₃ CH₂—C₆H₅ H A-429COCH₂Ph-3-CH₃ CH₂—C₆H₅ H A-430 COCH₂Ph-2-CH₃ CH₂—C₆H₅ H A-431COCH(CH₃)Ph CH₂—C₆H₅ H A-432 COCH(CH₃)-4-F CH₂—C₆H₅ H A-433COCH(CH₃)-4-CH₃ CH₂—C₆H₅ H A-434 COCH(CH₃)-3-CH₃ CH₂—C₆H₅ H A-435COCH(CH₃)-3-CH₃ CH₂—C₆H₅ H A-436 CF₃ CH₂—C₆H₅ H A-437 CHF₂ CH₂—C₆H₅ HA-438 CH₂CH₂OCH₃ CH₂—C₆H₅ H A-439 CH₂cPr CH₂—C₆H₅ H A-440 C₆H₅ CH₂—C₆H₅H A-441 CH₂—C₆H₅ CH₂—C₆H₅ H A-442 CH₂—C₆H₄-4-F CH₂—C₆H₅ H A-443CH₂—C₆H₄-4-CH₃ CH₂—C₆H₅ H A-444 CH₂—C₆H₄-3-CH₃ CH₂—C₆H₅ H A-445CH₂—C₆H₄-2-CH₃ CH₂—C₆H₅ H A-446 CH(CH₃)—C₆H₅ CH₂—C₆H₅ H A-447CH(CH₃)—C₆H₄-4-F CH₂—C₆H₅ H A-448 CH(CH₃)—C₆H₄-4-CH₃ CH₂—C₆H₅ H A-449CH(CH₃)—C₆H₄-3-CH₃ CH₂—C₆H₅ H A-450 CH(CH₃)—C₆H₄-2-CH₃ CH₂—C₆H₅ H A-451

CH₂—C₆H₅ H A-452

CH₂—C₆H₅ H A-453

CH₂—C₆H₅ H A-454 2-py CH₂—C₆H₅ H A-455 3-Py CH₂—C₆H₅ H A-456

CH₂—C₆H₅ H A-457

CH₂—C₆H₅ H A-458

CH₂—C₆H₅ H A-459

CH₂—C₆H₅ H A-460

CH₂—C₆H₅ H A-461 COCH₃ C₃H₇ CH₃ (cyclopropyl) A-462 COCH₂CH₃ C₃H₇ CH₃(cyclopropyl) A-463 COCH₂CH₂CH₃ C₃H₇ CH₃ (cyclopropyl) A-464 CO(CH₂)₃CH₃C₃H₇ CH₃ (cyclopropyl) A-465 CO(CH₂)₄CH₃ C₃H₇ CH₃ (cyclopropyl) A-466CO(CH₂)₅CH₃ C₃H₇ CH₃ (cyclopropyl) A-467 CO(CH₂)₆CH₃ C₃H₇ CH₃(cyclopropyl) A-468 COCCl₃ C₃H₇ CH₃ (cyclopropyl) A-469 COCH₂Cl C₃H₇ CH₃(cyclopropyl) A-470 COCH₂—N(CH₃)₂ C₃H₇ CH₃ (cyclopropyl) A-471 COPh C₃H₇CH₃ (cyclopropyl) A-472 COCH₂Ph C₃H₇ CH₃ (cyclopropyl) A-473 COCH₂Ph-4-FC₃H₇ CH₃ (cyclopropyl) A-474 COCH₂Ph-4-CH₃ C₃H₇ CH₃ (cyclopropyl) A-475COCH₂Ph-3-CH₃ C₃H₇ CH₃ (cyclopropyl) A-476 COCH₂Ph-2-CH₃ C₃H₇ CH₃(cyclopropyl) A-477 COCH(CH₃)Ph C₃H₇ CH₃ (cyclopropyl) A-478COCH(CH₃)-4-F C₃H₇ CH₃ (cyclopropyl) A-479 COCH(CH₃)-4-CH₃ C₃H₇ CH₃(cyclopropyl) A-480 COCH(CH₃)-3-CH₃ C₃H₇ CH₃ (cyclopropyl) A-481COCH(CH₃)-3-CH₃ C₃H₇ CH₃ (cyclopropyl) A-482 CF₃ C₃H₇ CH₃ (cyclopropyl)A-483 CHF₂ C₃H₇ CH₃ (cyclopropyl) A-484 CH₂CH₂OCH₃ C₃H₇ CH₃(cyclopropyl) A-485 CH₂cPr C₃H₇ CH₃ (cyclopropyl) A-486 C₆H₅ C₃H₇ CH₃(cyclopropyl) A-487 CH₂—C₆H₅ C₃H₇ CH₃ (cyclopropyl) A-488 CH₂—C₆H₄-4-FC₃H₇ CH₃ (cyclopropyl) A-489 CH₂—C₆H₄-4-CH₃ C₃H₇ CH₃ (cyclopropyl) A-490CH₂—C₆H₄-3-CH₃ C₃H₇ CH₃ (cyclopropyl) A-491 CH₂—C₆H₄-2-CH₃ C₃H₇ CH₃(cyclopropyl) A-492 CH(CH₃)—C₆H₅ C₃H₇ CH₃ (cyclopropyl) A-493CH(CH₃)—C₆H₄-4-F C₃H₇ CH₃ (cyclopropyl) A-494 CH(CH₃)—C₆H₄-4-CH₃ C₃H₇CH₃ (cyclopropyl) A-495 CH(CH₃)—C₆H₄-3-CH₃ C₃H₇ CH₃ (cyclopropyl) A-496CH(CH₃)—C₆H₄-2-CH₃ C₃H₇ CH₃ (cyclopropyl) A-497

C₃H₇ (cyclopropyl) CH₃ A-498

C₃H₇ (cyclopropyl) CH₃ A-499

C₃H₇ (cyclopropyl) CH₃ A-500 2-py C₃H₇ CH₃ (cyclopropyl) A-501 3-Py C₃H₇CH₃ (cyclopropyl) A-502

C₃H₇ (cyclopropyl) CH₃ A-503

C₃H₇ (cyclopropyl) CH₃ A-504

C₃H₇ (cyclopropyl) CH₃ A-505

C₃H₇ (cyclopropyl) CH₃ A-506

C₃H₇ (cyclopropyl) CH₃ A-507 COCH₃ i-C₃H₇ CH₃ A-508 COCH₂CH₃ i-C₃H₇ CH₃A-509 COCH₂CH₂CH₃ i-C₃H₇ CH₃ A-510 CO(CH₂)₃CH₃ i-C₃H₇ CH₃ A-511CO(CH₂)₄CH₃ i-C₃H₇ CH₃ A-512 CO(CH₂)₅CH₃ i-C₃H₇ CH₃ A-513 CO(CH₂)₆CH₃i-C₃H₇ CH₃ A-514 COCCl₃ i-C₃H₇ CH₃ A-515 COCH₂Cl i-C₃H₇ CH₃ A-516COCH₂—N(CH₃)₂ i-C₃H₇ CH₃ A-517 COPh i-C₃H₇ CH₃ A-518 COCH₂Ph i-C₃H₇ CH₃A-519 COCH₂Ph-4-F i-C₃H₇ CH₃ A-520 COCH₂Ph-4-CH₃ i-C₃H₇ CH₃ A-521COCH₂Ph-3-CH₃ i-C₃H₇ CH₃ A-522 COCH₂Ph-2-CH₃ i-C₃H₇ CH₃ A-523COCH(CH₃)Ph i-C₃H₇ CH₃ A-524 COCH(CH₃)-4-F i-C₃H₇ CH₃ A-525COCH(CH₃)-4-CH₃ i-C₃H₇ CH₃ A-526 COCH(CH₃)-3-CH₃ i-C₃H₇ CH₃ A-527COCH(CH₃)-3-CH₃ i-C₃H₇ CH₃ A-528 CF₃ i-C₃H₇ CH₃ A-529 CHF₂ i-C₃H₇ CH₃A-530 CH₂CH₂OCH₃ i-C₃H₇ CH₃ A-531 CH₂cPr i-C₃H₇ CH₃ A-532 C₆H₅ i-C₃H₇CH₃ A-533 CH₂—C₆H₅ i-C₃H₇ CH₃ A-534 CH₂—C₆H₄-4-F i-C₃H₇ CH₃ A-535CH₂—C₆H₄-4-CH₃ i-C₃H₇ CH₃ A-536 CH₂—C₆H₄-3-CH₃ i-C₃H₇ CH₃ A-537CH₂—C₆H₄-2-CH₃ i-C₃H₇ CH₃ A-538 CH(CH₃)—C₆H₅ i-C₃H₇ CH₃ A-539CH(CH₃)—C₆H₄-4-F i-C₃H₇ CH₃ A-540 CH(CH₃)—C₆H₄-4-CH₃ i-C₃H₇ CH₃ A-541CH(CH₃)—C₆H₄-3-CH₃ i-C₃H₇ CH₃ A-542 CH(CH₃)—C₆H₄-2-CH₃ i-C₃H₇ CH₃ A-543

i-C₃H₇ CH₃ A-544

i-C₃H₇ CH₃ A-545

i-C₃H₇ CH₃ A-546 2-py i-C₃H₇ CH₃ A-547 3-Py i-C₃H₇ CH₃ A-548

i-C₃H₇ CH₃ A-549

i-C₃H₇ CH₃ A-550

i-C₃H₇ CH₃ A-551

i-C₃H₇ CH₃ A-552

i-C₃H₇ CH₃ A-553 COCH₃ CH═CH₂ CH₃ A-554 COCH₂CH₃ CH═CH₂ CH₃ A-555COCH₂CH₂CH₃ CH═CH₂ CH₃ A-556 CO(CH₂)₃CH₃ CH═CH₂ CH₃ A-557 CO(CH₂)₄CH₃CH═CH₂ CH₃ A-558 CO(CH₂)₅CH₃ CH═CH₂ CH₃ A-559 CO(CH₂)₆CH₃ CH═CH₂ CH₃A-560 COCCl₃ CH═CH₂ CH₃ A-561 COCH₂Cl CH═CH₂ CH₃ A-562 COCH₂—N(CH₃)₂CH═CH₂ CH₃ A-563 COPh CH═CH₂ CH₃ A-564 COCH₂Ph CH═CH₂ CH₃ A-565COCH₂Ph-4-F CH═CH₂ CH₃ A-566 COCH₂Ph-4-CH₃ CH═CH₂ CH₃ A-567COCH₂Ph-3-CH₃ CH═CH₂ CH₃ A-568 COCH₂Ph-2-CH₃ CH═CH₂ CH₃ A-569COCH(CH₃)Ph CH═CH₂ CH₃ A-570 COCH(CH₃)-4-F CH═CH₂ CH₃ A-571COCH(CH₃)-4-CH₃ CH═CH₂ CH₃ A-572 COCH(CH₃)-3-CH₃ CH═CH₂ CH₃ A-573COCH(CH₃)-3-CH₃ CH═CH₂ CH₃ A-574 CF₃ CH═CH₂ CH₃ A-575 CHF₂ CH═CH₂ CH₃A-576 CH₂CH₂OCH₃ CH═CH₂ CH₃ A-577 CH₂cPr CH═CH₂ CH₃ A-578 C₆H₅ CH═CH₂CH₃ A-579 CH₂—C₆H₅ CH═CH₂ CH₃ A-580 CH₂—C₆H₄-4-F CH═CH₂ CH₃ A-581CH₂—C₆H₄-4-CH₃ CH═CH₂ CH₃ A-582 CH₂—C₆H₄-3-CH₃ CH═CH₂ CH₃ A-583CH₂—C₆H₄-2-CH₃ CH═CH₂ CH₃ A-584 CH(CH₃)—C₆H₅ CH═CH₂ CH₃ A-585CH(CH₃)—C₆H₄-4-F CH═CH₂ CH₃ A-586 CH(CH₃)—C₆H₄-4-CH₃ CH═CH₂ CH₃ A-587CH(CH₃)—C₆H₄-3-CH₃ CH═CH₂ CH₃ A-588 CH(CH₃)—C₆H₄-2-CH₃ CH═CH₂ CH₃ A-589

CH═CH₂ CH₃ A-590

CH═CH₂ CH₃ A-591

CH═CH₂ CH₃ A-592 2-py CH═CH₂ CH₃ A-593 3-Py CH═CH₂ CH₃ A-594

CH═CH₂ CH₃ A-595

CH═CH₂ CH₃ A-596

CH═CH₂ CH₃ A-597

CH═CH₂ CH₃ A-598

CH═CH₂ CH₃ A-599 COCH₃ CH₂CH═CH₂ CH₃ A-600 COCH₂CH₃ CH₂CH═CH₂ CH₃ A-601COCH₂CH₂CH₃ CH₂CH═CH₂ CH₃ A-602 CO(CH₂)₃CH₃ CH₂CH═CH₂ CH₃ A-603CO(CH₂)₄CH₃ CH₂CH═CH₂ CH₃ A-604 CO(CH₂)₅CH₃ CH₂CH═CH₂ CH₃ A-605CO(CH₂)₆CH₃ CH₂CH═CH₂ CH₃ A-606 COCCl₃ CH₂CH═CH₂ CH₃ A-607 COCH₂ClCH₂CH═CH₂ CH₃ A-608 COCH₂—N(CH₃)₂ CH₂CH═CH₂ CH₃ A-609 COPh CH₂CH═CH₂ CH₃A-610 COCH₂Ph CH₂CH═CH₂ CH₃ A-611 COCH₂Ph-4-F CH₂CH═CH₂ CH₃ A-612COCH₂Ph-4-CH₃ CH₂CH═CH₂ CH₃ A-613 COCH₂Ph-3-CH₃ CH₂CH═CH₂ CH₃ A-614COCH₂Ph-2-CH₃ CH₂CH═CH₂ CH₃ A-615 COCH(CH₃)Ph CH₂CH═CH₂ CH₃ A-616COCH(CH₃)-4-F CH₂CH═CH₂ CH₃ A-617 COCH(CH₃)-4-CH₃ CH₂CH═CH₂ CH₃ A-618COCH(CH₃)-3-CH₃ CH₂CH═CH₂ CH₃ A-619 COCH(CH₃)-3-CH₃ CH₂CH═CH₂ CH₃ A-620CF₃ CH₂CH═CH₂ CH₃ A-621 CHF₂ CH₂CH═CH₂ CH₃ A-622 CH₂CH₂OCH₃ CH₂CH═CH₂CH₃ A-623 CH₂cPr CH₂CH═CH₂ CH₃ A-624 C₆H₅ CH₂CH═CH₂ CH₃ A-625 CH₂—C₆H₅CH₂CH═CH₂ CH₃ A-626 CH₂—C₆H₄-4-F CH₂CH═CH₂ CH₃ A-627 CH₂—C₆H₄-4-CH₃CH₂CH═CH₂ CH₃ A-628 CH₂—C₆H₄-3-CH₃ CH₂CH═CH₂ CH₃ A-629 CH₂—C₆H₄-2-CH₃CH₂CH═CH₂ CH₃ A-630 CH(CH₃)—C₆H₅ CH₂CH═CH₂ CH₃ A-631 CH(CH₃)—C₆H₄-4-FCH₂CH═CH₂ CH₃ A-632 CH(CH₃)—C₆H₄-4-CH₃ CH₂CH═CH₂ CH₃ A-633CH(CH₃)—C₆H₄-3-CH₃ CH₂CH═CH₂ CH₃ A-634 CH(CH₃)—C₆H₄-2-CH₃ CH₂CH═CH₂ CH₃A-635

CH₂CH═CH₂ CH₃ A-636

CH₂CH═CH₂ CH₃ A-637

CH₂CH═CH₂ CH₃ A-638 2-py CH₂CH═CH₂ CH₃ A-639 3-Py CH₂CH═CH₂ CH₃ A-640

CH₂CH═CH₂ CH₃ A-641

CH₂CH═CH₂ CH₃ A-642

CH₂CH═CH₂ CH₃ A-643

CH₂CH═CH₂ CH₃ A-644

CH₂CH═CH₂ CH₃ A-645 COCH₃ C₆H₅ CH₃ A-646 COCH₂CH₃ C₆H₅ CH₃ A-647COCH₂CH₂CH₃ C₆H₅ CH₃ A-648 CO(CH₂)₃CH₃ C₆H₅ CH₃ A-649 CO(CH₂)₄CH₃ C₆H₅CH₃ A-650 CO(CH₂)₅CH₃ C₆H₅ CH₃ A-651 CO(CH₂)₆CH₃ C₆H₅ CH₃ A-652 COCCl₃C₆H₅ CH₃ A-653 COCH₂Cl C₆H₅ CH₃ A-654 COCH₂—N(CH₃)₂ C₆H₅ CH₃ A-655 COPhC₆H₅ CH₃ A-656 COCH₂Ph C₆H₅ CH₃ A-657 COCH₂Ph-4-F C₆H₅ CH₃ A-658COCH₂Ph-4-CH₃ C₆H₅ CH₃ A-659 COCH₂Ph-3-CH₃ C₆H₅ CH₃ A-660 COCH₂Ph-2-CH₃C₆H₅ CH₃ A-661 COCH(CH₃)Ph C₆H₅ CH₃ A-662 COCH(CH₃)-4-F C₆H₅ CH₃ A-663COCH(CH₃)-4-CH₃ C₆H₅ CH₃ A-664 COCH(CH₃)-3-CH₃ C₆H₅ CH₃ A-665COCH(CH₃)-3-CH₃ C₆H₅ CH₃ A-666 CF₃ C₆H₅ CH₃ A-667 CHF₂ C₆H₅ CH₃ A-668CH₂CH₂OCH₃ C₆H₅ CH₃ A-669 CH₂cPr C₆H₅ CH₃ A-670 C₆H₅ C₆H₅ CH₃ A-671CH₂—C₆H₅ C₆H₅ CH₃ A-672 CH₂—C₆H₄-4-F C₆H₅ CH₃ A-673 CH₂—C₆H₄-4-CH₃ C₆H₅CH₃ A-674 CH₂—C₆H₄-3-CH₃ C₆H₅ CH₃ A-675 CH₂—C₆H₄-2-CH₃ C₆H₅ CH₃ A-676CH(CH₃)—C₆H₅ C₆H₅ CH₃ A-677 CH(CH₃)—C₆H₄-4-F C₆H₅ CH₃ A-678CH(CH₃)—C₆H₄-4-CH₃ C₆H₅ CH₃ A-679 CH(CH₃)—C₆H₄-3-CH₃ C₆H₅ CH₃ A-680CH(CH₃)—C₆H₄-2-CH₃ C₆H₅ CH₃ A-681

C₆H₅ CH₃ A-682

C₆H₅ CH₃ A-683

C₆H₅ CH₃ A-684 2-py C₆H₅ CH₃ A-685 3-py C₆H₅ CH₃ A-686

C₆H₅ CH₃ A-687

C₆H₅ CH₃ A-688

C₆H₅ CH₃ A-689

C₆H₅ CH₃ A-690

C₆H₅ CH₃ A-691 COCH₃ CH₂C₆H₅ CH₃ A-692 COCH₂CH₃ CH₂C₆H₅ CH₃ A-693COCH₂CH₂CH₃ CH₂C₆H₅ CH₃ A-694 CO(CH₂)₃CH₃ CH₂C₆H₅ CH₃ A-695 CO(CH₂)₄CH₃CH₂C₆H₅ CH₃ A-696 CO(CH₂)₅CH₃ CH₂C₆H₅ CH₃ A-697 CO(CH₂)₆CH₃ CH₂C₆H₅ CH₃A-698 COCCl₃ CH₂C₆H₅ CH₃ A-699 COCH₂Cl CH₂C₆H₅ CH₃ A-700 COCH₂—N(CH₃)₂CH₂C₆H₅ CH₃ A-701 COPh CH₂C₆H₅ CH₃ A-702 COCH₂Ph CH₂C₆H₅ CH₃ A-703COCH₂Ph-4-F CH₂C₆H₅ CH₃ A-704 COCH₂Ph-4-CH₃ CH₂C₆H₅ CH₃ A-705COCH₂Ph-3-CH₃ CH₂C₆H₅ CH₃ A-706 COCH₂Ph-2-CH₃ CH₂C₆H₅ CH₃ A-707COCH(CH₃)Ph CH₂C₆H₅ CH₃ A-708 COCH(CH₃)-4-F CH₂C₆H₅ CH₃ A-709COCH(CH₃)-4-CH₃ CH₂C₆H₅ CH₃ A-710 COCH(CH₃)-3-CH₃ CH₂C₆H₅ CH₃ A-711COCH(CH₃)-3-CH₃ CH₂C₆H₅ CH₃ A-712 CF₃ CH₂C₆H₅ CH₃ A-713 CHF₂ CH₂C₆H₅ CH₃A-714 CH₂CH₂OCH₃ CH₂C₆H₅ CH₃ A-715 CH₂cPr CH₂C₆H₅ CH₃ A-716 C₆H₅ CH₂C₆H₅CH₃ A-717 CH₂—C₆H₅ CH₂C₆H₅ CH₃ A-718 CH₂—C₆H₄-4-F CH₂C₆H₅ CH₃ A-719CH₂—C₆H₄-4-CH₃ CH₂C₆H₅ CH₃ A-720 CH₂—C₆H₄-3-CH₃ CH₂C₆H₅ CH₃ A-721CH₂—C₆H₄-2-CH₃ CH₂C₆H₅ CH₃ A-722 CH(CH₃)—C₆H₅ CH₂C₆H₅ CH₃ A-723CH(CH₃)—C₆H₄-4-F CH₂C₆H₅ CH₃ A-724 CH(CH₃)—C₆H₄-4-CH₃ CH₂C₆H₅ CH₃ A-725CH(CH₃)—C₆H₄-3-CH₃ CH₂C₆H₅ CH₃ A-726 CH(CH₃)—C₆H₄-2-CH₃ CH₂C₆H₅ CH₃A-727

CH₂C₆H₅ CH₃ A-728

CH₂C₆H₅ CH₃ A-729

CH₂C₆H₅ CH₃ A-730 2-py CH₂C₆H₅ CH₃ A-731 3-py CH₂C₆H₅ CH₃ A-732

CH₂C₆H₅ CH₃ A-733

CH₂C₆H₅ CH₃ A-734

CH₂C₆H₅ CH₃ A-735

CH₂C₆H₅ CH₃ A-736

CH₂C₆H₅ CH₃ A-737 COCH₃

A-738 COCH₂CH₃

A-739 COCH₂CH₂CH₃

A-740 CO(CH₂)₃CH₃

A-741 CO(CH₂)₄CH₃

A-742 CO(CH₂)₅CH₃

A-743 CO(CH₂)₆CH₃

A-744 COCCl₃

A-745 COCH₂Cl

A-746 COCH₂—N(CH₃)₂

A-747 COPh

A-748 COCH₂Ph

A-749 COCH₂Ph-4-F

A-750 COCH₂Ph-4-CH₃

A-751 COCH₂Ph-3-CH₃

A-752 COCH₂Ph-2-CH₃

A-753 COCH(CH₃)Ph

A-754 COCH(CH₃)-4-F

A-755 COCH(CH₃)-4-CH₃

A-756 COCH(CH₃)-3-CH₃

A-757 COCH(CH₃)-3-CH₃

A-758 CF₃

A-759 CHF₂

A-760 CH₂CH₂OCH₃

A-761 CH₂cPr

A-762 C₆H₅

A-763 CH₂—C₆H₅

A-764 CH₂—C₆H₄-4-F

A-765 CH₂—C₆H₄-4-CH₃

A-766 CH₂—C₆H₄-3-CH₃

A-767 CH₂—C₆H₄-2-CH₃

A-768 CH(CH₃)—C₆H₅

A-769 CH(CH₃)—C₆H₄-4-F

A-770 CH(CH₃)—C₆H₄-4-CH₃

A-771 CH(CH₃)—C₆H₄-3-CH₃

A-772 CH(CH₃)—C₆H₄-2-CH₃

A-773

A-774

A-775

A-776 2-py

A-777 3-py

A-778

A-779

A-780

A-781

A-782

A-783 COCH₃

A-784 COCH₂CH₃

A-785 COCH₂CH₂CH₃

A-786 CO(CH₂)₃CH₃

A-787 CO(CH₂)₄CH₃

A-788 CO(CH₂)₅CH₃

A-789 CO(CH₂)₆CH₃

A-790 COCCl₃

A-791 COCH₂Cl

A-792 COCH₂—N(CH₃)₂

A-793 COPh

A-794 COCH₂Ph

A-795 COCH₂Ph-4-F

A-796 COCH₂Ph-4-CH₃

A-797 COCH₂Ph-3-CH₃

A-798 COCH₂Ph-2-CH₃

A-799 COCH(CH₃)Ph

A-800 COCH(CH₃)-4-F

A-801 COCH(CH₃)-4-CH₃

A-802 COCH(CH₃)-3-CH₃

A-803 COCH(CH₃)-3-CH₃

A-804 CF₃

A-805 CHF₂

A-806 CH₂CH₂OCH₃

A-807 CH₂cPr

A-808 C₆H₅

A-809 CH₂—C₆H₅

A-810 CH₂—C₆H₄-4-F

A-811 CH₂—C₆H₄-4-CH₃

A-812 CH₂—C₆H₄-3-CH₃

A-813 CH₂—C₆H₄-2-CH₃

A-814 CH(CH₃)—C₆H₅

A-815 CH(CH₃)—C₆H₄-4-F

A-816 CH(CH₃)—C₆H₄-4-CH₃

A-817 CH(CH₃)—C₆H₄-3-CH₃

A-818 CH(CH₃)—C₆H₄-2-CH₃

A-819

A-820

A-821

A-822 2-py

A-823 3-py

A-824

A-825

A-826

A-827

A-828

A-829 COCH₃

A-830 COCH₂CH₃

A-831 COCH₂CH₂CH₃

A-832 CO(CH₂)₃CH₃

A-833 CO(CH₂)₄CH₃

A-834 CO(CH₂)₅CH₃

A-835 CO(CH₂)₆CH₃

A-836 COCCl₃

A-837 COCH₂Cl

A-838 COCH₂—N(CH₃)₂

A-839 COPh

A-840 COCH₂Ph

A-841 COCH₂Ph-4-F

A-842 COCH₂Ph-4-CH₃

A-843 COCH₂Ph-3-CH₃

A-844 COCH₂Ph-2-CH₃

A-845 COCH(CH₃)Ph

A-846 COCH(CH₃)-4-F

A-847 COCH(CH₃)-4-CH₃

A-848 COCH(CH₃)-3-CH₃

A-849 COCH(CH₃)-3-CH₃

A-850 CF₃

A-851 CHF₂

A-852 CH₂CH₂OCH₃

A-853 CH₂cPr

A-854 C₆H₅

A-855 CH₂—C₆H₅

A-856 CH₂—C₆H₄-4-F

A-857 CH₂—C₆H₄-4-CH₃

A-858 CH₂—C₆H₄-3-CH₃

A-859 CH₂—C₆H₄-2-CH₃

A-860 CH(CH₃)—C₆H₅

A-861 CH(CH₃)—C₆H₄-4-F

A-862 CH(CH₃)—C₆H₄-4-CH₃

A-863 CH(CH₃)—C₆H₄-3-CH₃

A-864 CH(CH₃)—C₆H₄-2-CH₃

A-865

A-866

A-867

A-868 2-py

A-869 3-py

A-870

A-871

A-872

A-873

A-874

Particular embodiments of the compounds I are the following compounds:III-A, III-B, III-C, III-D, III-E, III-F, III-G, III-H, III-I; IV-A,IV-B, IV-C, IV-D, IV-E, IV-F, IV-G, IV-H, IV-I. In these formulae, thesubstituents R¹, R², R⁴ and Q³ are independently as defined in claim 1or preferably defined below:

Table 3-1 Compounds of the formula III-A, III-B, III-C, II-D, II-E,III-F, II-G, III-H, III-I in which the meaning for the combination ofQ¹, Q² and Q³ for each individual compound corresponds in each case toone line of Table B (compounds III-A.3-1.B-1 to III-A.3-1.B-230,III-B.3-1.B-1 to III-B.3-1.B-230, III-C.3-1.B-1 to III-C.3-1.B-230,III-D.3-1.B-1 to III-D.3-1.B-230, III-E.3-1.B-1 to III-E.3-1.B-230,III-F.3-1.B-1 to III-F.3-1.B-230, III-G.3-1.B-1 to III-G.3-1.B-230,III-H.3-1.B-1 to III-H.3-1.B-230, III-I.3-1B-1 to III-I.3-1.B-230).

Table 4-1 Compounds of the formula IV-A, IV-B, IV-C, IV-D, IV-E, IV-F,IV-G, IV-H, IV-I in which the meaning for the combination of Q¹, Q² andQ³ for each individual compound corresponds in each case to one line ofTable B (compounds IV-A.4-1.B-1 to IV-A.4-1.B-230, IV-B.4-1.B-1 toIV-B.4-1.B-230, IV-C.4-1.B-1 to IV-C.4-1.B-230, IV-D.4-1.B-1 toIV-D.4-1.B-230, IV-E.4-1.B-1 to IV-E.4-1.B-230, IV-F.4-1.B-1 toIV-F.4-1.B-230, IV-G.4-1.B-1 to IV-G.4-1.B-230, IV-H.4-1.B-1 toIV-H.4-1.B-230, IV-I.4-1.B-1 to IV-I.4-1.B-230).

TABLE B No. Q³ R¹ R² R⁴ B-1 COCH₃ CH₃ CH₃ H B-2 COCH₂CH₃ CH₃ CH₃ H B-3COCH₂CH₂CH₃ CH₃ CH₃ H B-4 CO(CH₂)₃CH₃ CH₃ CH₃ H B-5 CO(CH₂)₄CH₃ CH₃ CH₃H B-6 CO(CH₂)₅CH₃ CH₃ CH₃ H B-7 CO(CH₂)₆CH₃ CH₃ CH₃ H B-8 COCCl₃ CH₃ CH₃H B-9 COCH₂Cl CH₃ CH₃ H B-10 COCH₂—N(CH₃)₂ CH₃ CH₃ H B-11 COPh CH₃ CH₃ HB-12 COCH₂Ph CH₃ CH₃ H B-13 COCH₂Ph-4-F CH₃ CH₃ H B-14 COCH₂Ph-4-CH₃ CH₃CH₃ H B-15 COCH₂Ph-3-CH₃ CH₃ CH₃ H B-16 COCH₂Ph-2-CH₃ CH₃ CH₃ H B-17COCH(CH₃)Ph CH₃ CH₃ H B-18 COCH(CH₃)-4-F CH₃ CH₃ H B-19 COCH(CH₃)-4-CH₃CH₃ CH₃ H B-20 COCH(CH₃)-3-CH₃ CH₃ CH₃ H B-21 COCH(CH₃)-3-CH₃ CH₃ CH₃ HB-22 CF₃ CH₃ CH₃ H B-23 CHF₂ CH₃ CH₃ H B-24 CH₂CH₂OCH₃ CH₃ CH₃ H B-25CH₂cPr CH₃ CH₃ H B-26 C₆H₅ CH₃ CH₃ H B-27 CH₂—C₆H₅ CH₃ CH₃ H B-28CH₂—C₆H₄-4-F CH₃ CH₃ H B-29 CH₂—C₆H₄-4-CH₃ CH₃ CH₃ H B-30 CH₂—C₆H₄-3-CH₃CH₃ CH₃ H B-31 CH₂—C₆H₄-2-CH₃ CH₃ CH₃ H B-32 CH(CH₃)—C₆H₅ CH₃ CH₃ H B-33CH(CH₃)—C₆H₄-4-F CH₃ CH₃ H B-34 CH(CH₃)—C₆H₄-4-CH₃ CH₃ CH₃ H B-35CH(CH₃)—C₆H₄-3-CH₃ CH₃ CH₃ H B-36 CH(CH₃)—C₆H₄-2-CH₃ CH₃ CH₃ H B-37

CH₃ CH₃ H B-38

CH₃ CH₃ H B-39

CH₃ CH₃ H B-40 2-py CH₃ CH₃ H B-41 3-py CH₃ CH₃ H B-42

CH₃ CH₃ H B-43

CH₃ CH₃ H B-44

CH₃ CH₃ H B-45

CH₃ CH₃ H B-46

CH₃ CH₃ H B-47 COCH₃ CH₃ CH₃ CH₃ B-48 COCH₂CH₃ CH₃ CH₃ CH₃ B-49COCH₂CH₂CH₃ CH₃ CH₃ CH₃ B-50 CO(CH₂)₃CH₃ CH₃ CH₃ CH₃ B-51 CO(CH₂)₄CH₃CH₃ CH₃ CH₃ B-52 CO(CH₂)₅CH₃ CH₃ CH₃ CH₃ B-53 CO(CH₂)₆CH₃ CH₃ CH₃ CH₃B-54 COCCl₃ CH₃ CH₃ CH₃ B-55 COCH₂Cl CH₃ CH₃ CH₃ B-56 COCH₂—N(CH₃)₂ CH₃CH₃ CH₃ B-57 COPh CH₃ CH₃ CH₃ B-58 COCH₂Ph CH₃ CH₃ CH₃ B-59 COCH₂Ph-4-FCH₃ CH₃ CH₃ B-60 COCH₂Ph-4-CH₃ CH₃ CH₃ CH₃ B-61 COCH₂Ph-3-CH₃ CH₃ CH₃CH₃ B-62 COCH₂Ph-2-CH₃ CH₃ CH₃ CH₃ B-63 COCH(CH₃)Ph CH₃ CH₃ CH₃ B-64COCH(CH₃)-4-F CH₃ CH₃ CH₃ B-65 COCH(CH₃)-4-CH₃ CH₃ CH₃ CH₃ B-66COCH(CH₃)-3-CH₃ CH₃ CH₃ CH₃ B-67 COCH(CH₃)-3-CH₃ CH₃ CH₃ CH₃ B-68 CF₃CH₃ CH₃ CH₃ B-69 CHF₂ CH₃ CH₃ CH₃ B-70 CH₂CH₂OCH₃ CH₃ CH₃ CH₃ B-71CH₂cPr CH₃ CH₃ CH₃ B-72 C₆H₅ CH₃ CH₃ CH₃ B-73 CH₂—C₆H₅ CH₃ CH₃ CH₃ B-74CH₂—C₆H₄-4-F CH₃ CH₃ CH₃ B-75 CH₂—C₆H₄-4-CH₃ CH₃ CH₃ CH₃ B-76CH₂—C₆H₄-3-CH₃ CH₃ CH₃ CH₃ B-77 CH₂—C₆H₄-2-CH₃ CH₃ CH₃ CH₃ B-78CH(CH₃)—C₆H₅ CH₃ CH₃ CH₃ B-79 CH(CH₃)—C₆H₄-4-F CH₃ CH₃ CH₃ B-80CH(CH₃)—C₆H₄-4-CH₃ CH₃ CH₃ CH₃ B-81 CH(CH₃)—C₆H₄-3-CH₃ CH₃ CH₃ CH₃ B-82CH(CH₃)—C₆H₄-2-CH₃ CH₃ CH₃ CH₃ B-83

CH₃ CH₃ CH₃ B-84

CH₃ CH₃ CH₃ B-85

CH₃ CH₃ CH₃ B-86 2-py CH₃ CH₃ CH₃ B-87 3-py CH₃ CH₃ CH₃ B-88

CH₃ CH₃ CH₃ B-89

CH₃ CH₃ CH₃ B-90

CH₃ CH₃ CH₃ B-91

CH₃ CH₃ CH₃ B-92

CH₃ CH₃ CH₃ B-93 COCH₃ CH₃ CHF₂ H B-94 COCH₂CH₃ CH₃ CHF₂ H B-95COCH₂CH₂CH₃ CH₃ CHF₂ H B-96 CO(CH₂)₃CH₃ CH₃ CHF₂ H B-97 CO(CH₂)₄CH₃ CH₃CHF₂ H B-98 CO(CH₂)₅CH₃ CH₃ CHF₂ H B-99 CO(CH₂)₆CH₃ CH₃ CHF₂ H B-100COCCl₃ CH₃ CHF₂ H B-101 COCH₂Cl CH₃ CHF₂ H B-102 COCH₂—N(CH₃)₂ CH₃ CHF₂H B-103 COPh CH₃ CHF₂ H B-104 COCH₂Ph CH₃ CHF₂ H B-105 COCH₂Ph-4-F CH₃CHF₂ H B-106 COCH₂Ph-4-CH₃ CH₃ CHF₂ H B-107 COCH₂Ph-3-CH₃ CH₃ CHF₂ HB-108 COCH₂Ph-2-CH₃ CH₃ CHF₂ H B-109 COCH(CH₃)Ph CH₃ CHF₂ H B-110COCH(CH₃)-4-F CH₃ CHF₂ H B-111 COCH(CH₃)-4-CH₃ CH₃ CHF₂ H B-112COCH(CH₃)-3-CH₃ CH₃ CHF₂ H B-113 COCH(CH₃)-3-CH₃ CH₃ CHF₂ H B-114 CF₃CH₃ CHF₂ H B-115 CHF₂ CH₃ CHF₂ H B-116 CH₂CH₂OCH₃ CH₃ CHF₂ H B-117CH₂cPr CH₃ CHF₂ H B-118 C₆H₅ CH₃ CHF₂ H B-119 CH₂—C₆H₅ CH₃ CHF₂ H B-120CH₂—C₆H₄-4-F CH₃ CHF₂ H B-121 CH₂—C₆H₄-4-CH₃ CH₃ CHF₂ H B-122CH₂—C₆H₄-3-CH₃ CH₃ CHF₂ H B-123 CH₂—C₆H₄-2-CH₃ CH₃ CHF₂ H B-124CH(CH₃)—C₆H₅ CH₃ CHF₂ H B-125 CH(CH₃)—C₆H₄-4-F CH₃ CHF₂ H B-126CH(CH₃)—C₆H₄-4-CH₃ CH₃ CHF₂ H B-127 CH(CH₃)—C₆H₄-3-CH₃ CH₃ CHF₂ H B-128CH(CH₃)—C₆H₄-2-CH₃ CH₃ CHF₂ H B-129

CH₃ CHF₂ H B-130

CH₃ CHF₂ H B-131

CH₃ CHF₂ H B-132 2-py CH₃ CHF₂ H B-133 3-Py CH₃ CHF₂ H B-134

CH₃ CHF₂ H B-135

CH₃ CHF₂ H B-136

CH₃ CHF₂ H B-137

CH₃ CHF₂ H B-138

CH₃ CHF₂ H B-139 COCH₃ CH₃ OCH₃ H B-140 COCH₂CH₃ CH₃ OCH₃ H B-141COCH₂CH₂CH₃ CH₃ OCH₃ H B-142 CO(CH₂)₃CH₃ CH₃ OCH₃ H B-143 CO(CH₂)₄CH₃CH₃ OCH₃ H B-144 CO(CH₂)₅CH₃ CH₃ OCH₃ H B-145 CO(CH₂)₆CH₃ CH₃ OCH₃ HB-146 COCCl₃ CH₃ OCH₃ H B-147 COCH₂Cl CH₃ OCH₃ H B-148 COCH₂—N(CH₃)₂ CH₃OCH₃ H B-149 COPh CH₃ OCH₃ H B-150 COCH₂Ph CH₃ OCH₃ H B-151 COCH₂Ph-4-FCH₃ OCH₃ H B-152 COCH₂Ph-4-CH₃ CH₃ OCH₃ H B-153 COCH₂Ph-3-CH₃ CH₃ OCH₃ HB-154 COCH₂Ph-2-CH₃ CH₃ OCH₃ H B-155 COCH(CH₃)Ph CH₃ OCH₃ H B-156COCH(CH₃)-4-F CH₃ OCH₃ H B-157 COCH(CH₃)-4-CH₃ CH₃ OCH₃ H B-158COCH(CH₃)-3-CH₃ CH₃ OCH₃ H B-159 COCH(CH₃)-3-CH₃ CH₃ OCH₃ H B-160 CF₃CH₃ OCH₃ H B-161 CHF₂ CH₃ OCH₃ H B-162 CH₂CH₂OCH₃ CH₃ OCH₃ H B-163CH₂cPr CH₃ OCH₃ H B-164 C₆H₅ CH₃ OCH₃ H B-165 CH₂—C₆H₅ CH₃ OCH₃ H B-166CH₂—C₆H₄-4-F CH₃ OCH₃ H B-167 CH₂—C₆H₄-4-CH₃ CH₃ OCH₃ H B-168CH₂—C₆H₄-3-CH₃ CH₃ OCH₃ H B-169 CH₂—C₆H₄-2-CH₃ CH₃ OCH₃ H B-170CH(CH₃)—C₆H₅ CH₃ OCH₃ H B-171 CH(CH₃)—C₆H₄-4-F CH₃ OCH₃ H B-172CH(CH₃)—C₆H₄-4-CH₃ CH₃ OCH₃ H B-173 CH(CH₃)—C₆H₄-3-CH₃ CH₃ OCH₃ H B-174CH(CH₃)—C₆H₄-2-CH₃ CH₃ OCH₃ H B-175

CH₃ OCH₃ H B-176

CH₃ OCH₃ H B-177

CH₃ OCH₃ H B-178 2-py CH₃ OCH₃ H B-179 3-py B-180

CH₃ OCH₃ H B-181

CH₃ OCH₃ H B-182

CH₃ OCH₃ H B-183

CH₃ OCH₃ H B-184

CH₃ OCH₃ H B-185 COCH₃ OCH₃ CHF₂ H B-186 COCH₂CH₃ OCH₃ CHF₂ H B-187COCH₂CH₂CH₃ OCH₃ CHF₂ H B-188 CO(CH₂)₃CH₃ OCH₃ CHF₂ H B-189 CO(CH₂)₄CH₃OCH₃ CHF₂ H B-190 CO(CH₂)₅CH₃ OCH₃ CHF₂ H B-191 CO(CH₂)₆CH₃ OCH₃ CHF₂ HB-192 COCCl₃ OCH₃ CHF₂ H B-193 COCH₂Cl OCH₃ CHF₂ H B-194 COCH₂—N(CH₃)₂OCH₃ CHF₂ H B-195 COPh OCH₃ CHF₂ H B-196 COCH₂Ph OCH₃ CHF₂ H B-197COCH₂Ph-4-F OCH₃ CHF₂ H B-198 COCH₂Ph-4-CH₃ OCH₃ CHF₂ H B-199COCH₂Ph-3-CH₃ OCH₃ CHF₂ H B-200 COCH₂Ph-2-CH₃ OCH₃ CHF₂ H B-201COCH(CH₃)Ph OCH₃ CHF₂ H B-202 COCH(CH₃)-4-F OCH₃ CHF₂ H B-203COCH(CH₃)-4-CH₃ OCH₃ CHF₂ H B-204 COCH(CH₃)-3-CH₃ OCH₃ CHF₂ H B-205COCH(CH₃)-3-CH₃ OCH₃ CHF₂ H B-206 CF₃ OCH₃ CHF₂ H B-207 CHF₂ OCH₃ CHF₂ HB-208 CH₂CH₂OCH₃ OCH₃ CHF₂ H B-209 CH₂cPr OCH₃ CHF₂ H B-210 C₆H₅ OCH₃CHF₂ H B-211 CH₂—C₆H₅ OCH₃ CHF₂ H B-212 CH₂—C₆H₄-4-F OCH₃ CHF₂ H B-213CH₂—C₆H₄-4-CH₃ OCH₃ CHF₂ H B-214 CH₂—C₆H₄-3-CH₃ OCH₃ CHF₂ H B-215CH₂—C₆H₄-2-CH₃ OCH₃ CHF₂ H B-216 CH(CH₃)—C₆H₅ OCH₃ CHF₂ H B-217CH(CH₃)—C₆H₄-4-F OCH₃ CHF₂ H B-218 CH(CH₃)—C₆H₄-4-CH₃ OCH₃ CHF₂ H B-219CH(CH₃)—C₆H₄-3-CH₃ OCH₃ CHF₂ H B-220 CH(CH₃)—C₆H₄-2-CH₃ OCH₃ CHF₂ HB-221

OCH₃ CHF₂ H B-222

OCH₃ CHF₂ H B-223

OCH₃ CHF₂ H B-224 2-py OCH₃ CHF₂ H B-225 3-py OCH₃ CHF₂ H B-226

OCH₃ CHF₂ H B-227

OCH₃ CHF₂ H B-228

OCH₃ CHF₂ H B-229

OCH₃ CHF₂ H B-230

OCH₃ CHF₂ H

The compounds I and the compositions according to the invention,respectively, are suitable as fungicides. They are distinguished by anoutstanding effectiveness against a broad spectrum of phytopathogenicfungi, including soil-borne fungi, which derive especially from theclasses of the Plasmodiophoromycetes, Peronosporomycetes (syn.Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetesand Deuteromycetes (syn. Fungi imperfecti). Some are systemicallyeffective and they can be used in crop protection as foliar fungicides,fungicides for seed dressing and soil fungicides. Moreover, they aresuitable for controlling harmful fungi, which inter alia occur in woodor roots of plants.

The compounds I and the compositions according to the invention areparticularly important in the control of a multitude of phytopathogenicfungi on various cultivated plants, such as cereals, e. g. wheat, rye,barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet;fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears,plums, peaches, almonds, cherries, strawberries, raspberries,blackberries or gooseberries; leguminous plants, such as lentils, peas,alfalfa or soybeans; oil plants, such as rape, mustard, olives,sunflowers, coconut, cocoa beans, castor oil plants, oil palms, groundnuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiberplants, such as cotton, flax, hemp or jute; citrus fruit, such asoranges, lemons, grapefruits or mandarins; vegetables, such as spinach,lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes,cucurbits or paprika; lauraceous plants, such as avocados, cinnamon orcamphor; energy and raw material plants, such as corn, soybean, rape,sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines(table grapes and grapejuice grape vines); hop; turf; sweet leaf (alsocalled Stevia); natural rubber plants or ornamental and forestry plants,such as flowers, shrubs, broad-leaved trees or evergreens, e. g.conifers; and on the plant propagation material, such as seeds, and thecrop material of these plants.

Preferably, compounds I and compositions thereof, respectively are usedfor controlling a multitude of fungi on field crops, such as potatoessugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton,soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits;vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans orsquashes.

The term “plant propagation material” is to be understood to denote allthe generative parts of the plant such as seeds and vegetative plantmaterial such as cuttings and tubers (e. g. potatoes), which can be usedfor the multiplication of the plant. This includes seeds, roots, fruits,tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants,including seedlings and young plants, which are to be transplanted aftergermination or after emergence from soil. These young plants may also beprotected before transplantation by a total or partial treatment byimmersion or pouring.

Preferably, treatment of plant propagation materials with compounds Iand compositions thereof, respectively, is used for controlling amultitude of fungi on cereals, such as wheat, rye, barley and oats;rice, corn, cotton and soybeans.

The term “cultivated plants” is to be understood as including plantswhich have been modified by breeding, mutagenesis or genetic engineeringincluding but not limiting to agricultural biotech products on themarket or in development (cf. http://cera-gmc.org/, see GM crop databasetherein). Genetically modified plants are plants, which genetic materialhas been so modified by the use of recombinant DNA techniques that undernatural circumstances cannot readily be obtained by cross breeding,mutations or natural recombination. Typically, one or more genes havebeen integrated into the genetic material of a genetically modifiedplant in order to improve certain properties of the plant. Such geneticmodifications also include but are not limited to targetedpost-translational modification of protein(s), oligo- or polypeptides e.g. by glycosylation or polymer additions such as prenylated, acetylatedor farnesylated moieties or PEG moieties.

Plants that have been modified by breeding, mutagenesis or geneticengineering, e. g. have been rendered tolerant to applications ofspecific classes of herbicides, such as auxin herbicides such as dicambaor 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase(HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactatesynthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones;enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such asglyphosate; glutamine synthetase (GS) inhibitors such as glufosinate;protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitorssuch as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e.bromoxynil or ioxynil) herbicides as a result of conventional methods ofbreeding or genetic engineering. Furthermore, plants have been maderesistant to multiple classes of herbicides through multiple geneticmodifications, such as resistance to both glyphosate and glufosinate orto both glyphosate and a herbicide from another class such as ALSinhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.These herbicide resistance technologies are e. g. described in PestManagem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005,269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009,108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185;and references quoted therein. Several cultivated as soybean, cotton,corn, beets and rape, tolerant to herbicides such as glyphosate andglufosinate, some of which are commercially available under the tradenames RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance®(imidazolinone tolerant, BASF SE, Germany) and LibertyLink®(glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more insecticidal proteins,especially those known from the bacterial genus Bacillus, particularlyfrom Bacillus thuringiensis, such as b-endotoxins, e. g. CryIA(b),CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c;vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e. g.Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, suchas scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, suchStreptomycetes toxins, plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilbene synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, e. g. WO 02/015701). Further examples of such toxins orgenetically modified plants capable of synthesizing such toxins aredisclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO 03/18810 und WO 03/52073. The methods for producingsuch genetically modified plants are generally known to the personskilled in the art and are described, e. g. in the publicationsmentioned above. These insecticidal proteins contained in thegenetically modified plants impart to the plants producing theseproteins tolerance to harmful pests from all taxonomic groups ofarthropods, especially to beetles (Coeloptera), two-winged insects(Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).Genetically modified plants capable to synthesize one or moreinsecticidal proteins are, e. g., described in the publicationsmentioned above, and some of which are commercially available such asYieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus(corn cultivars producing Cry1Ab and Cry3Bb1 toxins), Starlink® (corncultivars producing the Cry9c toxin), Herculex® RW (corn cultivarsproducing Cry34Ab1, Cry35Ab1 and the enzymephosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cottoncultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivarsproducing the Cry1Ac toxin), Bollgard® II (cotton cultivars producingCry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing aVIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin);Bt-Xtra®, NatureGard®, KnockOut®, BiteGard, Protecta, Bt11 (e. g.Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivarsproducing the Cry1Ab toxin and PAT enyzme), MIR604 from Syngenta SeedsSAS, France (corn cultivars producing a modified version of the Cry3Atoxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium(corn cultivars producing the Cry3Bb1 toxin), IPC 531 from MonsantoEurope S.A., Belgium (cotton cultivars producing a modified version ofthe Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium(corn cultivars producing the Cry1F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe resistance or tolerance of those plants to bacterial, viral orfungal pathogens. Examples of such proteins are the so-called“pathogenesis-related proteins” (PR proteins, see, e. g. EP-A 392 225),plant disease resistance genes (e. g. potato cultivars, which expressresistance genes acting against Phytophthora infestans derived from theMexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potatocultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylvora). The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e. g. in the publicationsmentioned above.

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe productivity (e. g. bio mass production, grain yield, starchcontent, oil content or protein content), tolerance to drought, salinityor other growth-limiting environmental factors or tolerance to pests andfungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve human or animalnutrition, e. g. oil crops that produce health-promoting long-chainomega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera©rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve raw materialproduction, e. g. potatoes that produce increased amounts of amylopectin(e. g. Amflora® potato, BASF SE, Germany).

The compounds I and compositions thereof, respectively, are particularlysuitable for controlling the following plant diseases:

Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. candida)and sunflowers (e. g. A. tragopogonis); Alternaria spp. (Alternaria leafspot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A.tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A.alternata), tomatoes (e. g. A. solani or A. alternata) and wheat;Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. oncereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A.hordei on barley; Bipolaris and Drechslera spp. (teleomorph:Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northernleaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokiniana) oncereals and e. g. B. oryzae on rice and turfs; Blumeria (formerlyErysiphe) graminis (powdery mildew) on cereals (e. g. on wheat orbarley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: greymold) on fruits and berries (e. g. strawberries), vegetables (e. g.lettuce, carrots, celery and cabbages), rape, flowers, vines, forestryplants and wheat; Bremia lactucae (downy mildew) on lettuce;Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved treesand evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercosporaspp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C.zeae-maydis), rice, sugar beets (e. g. C. beticola), sugar cane,vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchil) and rice;Cladosporium spp. on tomatoes (e. g. C. fulvum. leaf mold) and cereals,e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) oncereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp.(leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph:B. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae);Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e.g. C. gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot),soft fruits, potatoes (e. g. C. coccodes black dot), beans (e. g. C.lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides);Corticium spp., e. g. C. sasakii(sheath blight) on rice; Corynesporacassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp.,e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit treecanker or young vine decline, teleomorph: Nectria or Neonectria spp.) onfruit trees, vines (e. g. C. liriodendri teleomorph: Neonectrialiriodendri Black Foot Disease) and ornamentals; Dematophora(teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans;Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans;Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. oncorn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e.g. D. tritici-repentis tan spot), rice and turf; Esca (dieback,apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F.mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremoniumchlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeriaobtusa; Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta:anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae (leafsmut) on rice; Epicoccum spp. (black mold) on wheat; Erysihe spp.(powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pisi),such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E.crucferarum); Eutypa lata (Eutypa canker or dieback, anamorph:Cytosporna lata, syn. Libertella blepharis) on fruit trees, vines andornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e.g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root orstem rot) on various plants, such as F. graminearum or F. culmorum (rootrot, scab or head blight) on cereals (e. g. wheat or barley), F.oxysporum on tomatoes, F. solani (f. sp. glycines now syn. F.virguliforme) and F. tucumaniae and F. brasillense each causing suddendeath syndrome on soybeans, and F. verticillloides on corn;Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley)and corn; Gibberella spp. on cereals (e. g. G. zeae) and rice (e. g. G.fujkuro Bakanae disease); Glomerella clingulata on vines, pome fruitsand other plants and G. gossypii on cotton; Grainstaining complex onrice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. onrosaceous plants and junipers, e. g. G. sabinae (rust) on pears;Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) oncorn, cereals and rice; Hemileia spp., e. g. H. vastatrix(coffee leafrust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) onvines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) onsoybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snowmold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powderymildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructcola and M.fructgena (bloom and twig blight, brown rot) on stone fruits and otherrosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruitsand ground nuts, such as e. g. M. graminicola (anamorph: Septoriatritici; Septoria blotch) on wheat or M. fijiensis (black Sigatokadisease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g.P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor),tobacco (P. tabacina) and soybeans (e. g. P. manshurica); Phakopsorapachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp.e. g. on vines (e. g. P. trachephila and P. tetraspora) and soybeans (e.g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape andcabbage and P. betae (root rot, leaf spot and damping-off) on sugarbeets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can andleaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph:Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn;Phytophthora spp. (wilt, root, leaf, fruit and stem root) on variousplants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e.g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P.infestans late blight) and broad-leaved trees (e. g. P. ramorum: suddenoak death); Plasmodiophora brasscae (club root) on cabbage, rape, radishand other plants; Plasmopara spp., e. g. P. viticola (grapevine downymildew) on vines and P. halstedii on sunflowers; Podosphaera spp.(powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g.P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such asbarley and wheat (P. graminis) and sugar beets (P. betae) and therebytransmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat or barley;Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensisoncucurbits or P. humili on hop; Pseudopezicua tracheiphila (red firedisease or ‘rotbrenner’, anamorph: Phialophora) on vines; Puccinia spp.(rusts) on various plants, e. g. P. triticina (brown or leaf rust), P.striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis(stem or black rust) or P. recondita (brown or leaf rust) on cereals,such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugarcane and P. asparagi on asparagus; Pyrenophora(anamorph: Drechslera)tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley;Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, riceblast) on rice and P. grisea on turf and cereals; Pythium spp.(damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers,soybeans, sugar beets, vegetables and various other plants (e. g. P.ulitimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni(Ramularia leaf spots, Physiological leaf spots) on barley and R.beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes,turf, corn, rape, potatoes, sugar beets, vegetables and various otherplants, e. g. R. solani (root and stem rot) on soybeans, R. solani(sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) onwheat or barley; Rhizopus stolonifer (black mold, soft rot) onstrawberries, carrots, cabbage, vines and tomatoes; Rhynchosporiumsecalis (scald) on barley, rye and triticale; Sarocladium oryzae and S.attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or whitemold) on vegetables and field crops, such as rape, sunflowers (e. g. S.sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum);Septoria spp. on various plants, e. g. S. glycines (brown spot) onsoybeans, S. tritici (Septoria blotch) on wheat and S. (syn.Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn.Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines;Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn.Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn,(e. g. S. relliana: head smut), sorghum und sugar cane; Sphaerothecafuliginea (powdery mildew) on cucurbits; Spongospora subterranea(powdery scab) on potatoes and thereby transmitted viral diseases;Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch,teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat;Synchytrium endobioticum on potatoes (potato wart disease); Taphrinaspp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni(plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco,pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn.Chalara elegans); Tilletia spp. (common bunt or stinking smut) oncereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T.controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) onbarley or wheat; Urocystis spp., e. g. U. occuita (stem smut) on rye;Uromyces spp. (rust) on vegetables, such as beans (e. g. U.appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae);Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae),corn (e. g. U. maydis corn smut) and sugar cane; Venturia spp. (scab) onapples (e. g. V. inaequalls) and pears; and Verticillium spp. (wilt) onvarious plants, such as fruits and ornamentals, vines, soft fruits,vegetables and field crops, e. g. V. dahliae on strawberries, rape,potatoes and tomatoes.

The compounds I and compositions thereof, respectively, are alsosuitable for controlling harmful fungi in the protection of storedproducts or harvest and in the protection of materials.

The term “protection of materials” is to be understood to denote theprotection of technical and non-living materials, such as adhesives,glues, wood, paper and paperboard, textiles, leather, paint dispersions,plastics, cooling lubricants, fiber or fabrics, against the infestationand destruction by harmful microorganisms, such as fungi and bacteria.As to the protection of wood and other materials, the particularattention is paid to the following harmful fungi: Ascomycetes such asOphiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophomaspp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.;Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllumspp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. andTyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporiumspp., Peniclllum spp., Trichoderma spp., Alternara spp., Paecilomycesspp. and Zygomycetes such as Mucor spp., and in addition in theprotection of stored products and harvest the following yeast fungi areworthy of note: Candida spp. and Saccharomyces cerevisae.

The method of treatment according to the invention can also be used inthe field of protecting stored products or harvest against attack offungi and microorganisms. According to the present invention, the term“stored products” is understood to denote natural substances of plant oranimal origin and their processed forms, which have been taken from thenatural life cycle and for which long-term protection is desired. Storedproducts of crop plant origin, such as plants or parts thereof, forexample stalks, leafs, tubers, seeds, fruits or grains, can be protectedin the freshly harvested state or in processed form, such as pre-dried,moistened, comminuted, ground, pressed or roasted, which process is alsoknown as post-harvest treatment. Also falling under the definition ofstored products is timber, whether in the form of crude timber, such asconstruction timber, electricity pylons and barriers, or in the form offinished articles, such as furniture or objects made from wood. Storedproducts of animal origin are hides, leather, furs, hairs and the like.The combinations according the present invention can preventdisadvantageous effects such as decay, discoloration or mold. Preferably“stored products” is understood to denote natural substances of plantorigin and their processed forms, more preferably fruits and theirprocessed forms, such as pomes, stone fruits, soft fruits and citrusfruits and their processed forms.

The compounds I and compositions thereof, respectively, may be used forimproving the health of a plant. The invention also relates to a methodfor improving plant health by treating a plant, its propagation materialand/or the locus where the plant is growing or is to grow with aneffective amount of compounds I and compositions thereof, respectively.

The term “plant health” is to be understood to denote a condition of theplant and/or its products which is determined by several indicatorsalone or in combination with each other such as yield (e. g. increasedbiomass and/or increased content of valuable ingredients), plant vigor(e. g. improved plant growth and/or greener leaves (“greening effect”)),quality (e. g. improved content or composition of certain ingredients)and tolerance to abiotic and/or biotic stress. The above identifiedindicators for the health condition of a plant may be interdependent ormay result from each other.

The compounds of formula I can be present in different crystalmodifications whose biological activity may differ. They are likewisesubject matter of the present invention.

The compounds I are employed as such or in form of compositions bytreating the fungi or the plants, plant propagation materials, such asseeds, soil, surfaces, materials or rooms to be protected from fungalattack with a fungicidally effective amount of the active substances.The application can be carried out both before and after the infectionof the plants, plant propagation materials, such as seeds, soil,surfaces, materials or rooms by the fungi.

Plant propagation materials may be treated with compounds I as such or acomposition comprising at least one compound I prophylactically eitherat or before planting or transplanting.

The invention also relates to agrochemical compositions comprising anauxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a fungicidally effective amount ofa compound I. The term “effective amount” denotes an amount of thecomposition or of the compounds I, which is sufficient for controllingharmful fungi on cultivated plants or in the protection of materials andwhich does not result in a substantial damage to the treated plants.Such an amount can vary in a broad range and is dependent on variousfactors, such as the fungal species to be controlled, the treatedcultivated plant or material, the climatic conditions and the specificcompound I used.

The compounds I, their N-oxides and salts can be converted intocustomary types of agrochemical compositions, e. g. solutions,emulsions, suspensions, dusts, powders, pastes, granules, pressings,capsules, and mixtures thereof. Examples for composition types aresuspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC),emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes,pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS),pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG),insecticidal articles (e. g. LN), as well as gel formulations for thetreatment of plant propagation materials such as seeds (e. g. GF). Theseand further compositions types are defined in the “Catalogue ofpesticide formulation types and international coding system”, TechnicalMonograph No. 2, 6^(th) Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or Knowles, New developments in crop protection product formulation,Agrow Reports DS243, T&F Informa, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers orfillers, surfactants, dispersants, emulsifiers, wetters, adjuvants,solubilizers, penetration enhancers, protective colloids, adhesionagents, thickeners, humectants, repellents, attractants, feedingstimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e. g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol,propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones,e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixturesthereof.

Suitable solid carriers or fillers are mineral earths, e. g. silicates,silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite,diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate,magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers,e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas;products of vegetable origin, e. g. cereal meal, tree bark meal, woodmeal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof. Such surfactants can be used asemulsifier, dispersant, solubilizer, wetter, penetration enhancer,protective colloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylaryl sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates offatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonatesof alkoxylated arylphenols, sulfonates of condensed naphthalenes,sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenesand alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examplesof sulfates are sulfates of fatty acids and oils, of ethoxylatedalkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acidesters. Examples of phosphates are phosphate esters. Examples ofcarboxylates are alkyl carboxylates, and carboxylated alcohol oralkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinyl amines or polyethylene amines.

Suitable adjuvants are compounds, which have a negligible or even nopesticidal activity themselves, and which improve the biologicalperformance of the compound I on the target. Examples are surfactants,mineral or vegetable oils, and other auxiliaries. Further examples arelisted by Knowles, Adjuvants and additives, Agrow Reports DS256, T&FInforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e. g. xanthan gum,carboxymethyl cellulose), inorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e. g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e. g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e. g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or syntheticwaxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-Soluble Concentrates (SL, LS)

10-60 wt % of a compound I and 5-15 wt % wetting agent (e. g. alcoholalkoxylates) are dissolved in water and/or in a water-soluble solvent(e. g. alcohols) ad 100 wt %. The active substance dissolves upondilution with water.

ii) Dispersible Concentrates (DC)

5-25 wt % of a compound I and 1-10 wt % dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad100 wt %. Dilution with water gives a dispersion.

iii) Emulsifiable Concentrates (EC)

15-70 wt % of a compound I and 5-10 wt % emulsifiers (e. g. calciumdodecylbenzenesulfonate and castor oil ethoxylate) are dissolved inwater-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I and 1-10 wt % emulsifiers (e. g. calciumdodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in20-40 wt % water-insoluble organic solvent (e. g. aromatic hydrocarbon).This mixture is introduced into water ad 100 wt % by means of anemulsifying machine and made into a homogeneous emulsion. Dilution withwater gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I are comminuted withaddition of 2-10 wt % dispersants and wetting agents (e. g. sodiumlignosulfonate and alcohol ethoxylate), 0.1-2 wt % thickener (e. g.xanthan gum) and water ad 100 wt % to give a fine active substancesuspension. Dilution with water gives a stable suspension of the activesubstance. For FS type composition up to 40 wt % binder (e. g. polyvinylalcohol) is added.

vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50-80 wt % of a compound I are ground finely with addition ofdispersants and wetting agents (e. g. sodium lignosulfonate and alcoholethoxylate) ad 100 wt % and prepared as water-dispersible orwater-soluble granules by means of technical appliances (e. g.extrusion, spray tower, fluidized bed). Dilution with water gives astable dispersion or solution of the active substance.

vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, WS)

50-80 wt % of a compound I are ground in a rotor-stator mill withaddition of 1-5 wt % dispersants (e. g. sodium lignosulfonate), 1-3 wt %wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g.silica gel) ad 100 wt %. Dilution with water gives a stable dispersionor solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of a compound I are comminuted withaddition of 3-10 wt % dispersants (e. g. sodium lignosulfonate), 1-5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt % togive a fine suspension of the active substance. Dilution with watergives a stable suspension of the active substance.

ix) Microemulsion (ME)

5-20 wt % of a compound I are added to 5-30 wt % organic solvent blend(e. g. fatty acid di-methyl amide and cyclohexanone), 10-25 wt %surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate),and water ad 100%. This mixture is stirred for 1 h to producespontaneously a thermodynamically stable microemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I, 0-40 wt % waterinsoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt %acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di-or triacrylate) are dispersed into an aqueous solution of a protectivecolloid (e. g. polyvinyl alcohol). Radical polymerization results in theformation of poly(meth)acrylate microcapsules. Alternatively, an oilphase comprising 5-50 wt % of a compound I according to the invention,0-40 wt % water insoluble organic solvent (e. g. aromatic hydrocarbon),and an isocyanate monomer (e. g. diphenylmethene-4,4′-diisocyanatae) aredispersed into an aqueous solution of a protective colloid (e. g.polyvinyl alcohol). The addition of a polyamine (e. g.hexamethylenediamine) results in the formation of polyureamicrocapsules. The monomers amount to 1-10 wt %. The wt % relate to thetotal CS composition.

xi) Dustable Powders (DP, DS)

1-10 wt % of a compound I are ground finely and mixed intimately withsolid carrier (e. g. finely divided kaolin) ad 100 wt %.

xii) Granules (GR, FG)

0.5-30 wt % of a compound I is ground finely and associated with solidcarrier (e. g. silicate) ad 100 wt %. Granulation is achieved byextrusion, spray-drying or fluidized bed.

xiii) Ultra-low volume liquids (UL)

1-50 wt % of a compound I are dissolved in organic solvent (e. g.aromatic hydrocarbon) ad 100 wt %.

The compositions types i) to xiii) may optionally comprise furtherauxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, more preferably between 1 and 70%, andin particular between 10 and 60%, by weight of active substance. Theactive substances are employed in a purity of from 90% to 100%,preferably from 95% to 100% (according to NMR spectrum).

For the purposes of treatment of plant propagation materials,particularly seeds, solutions for seed treatment (LS), Suspoemulsions(SE), flowable concentrates (FS), powders for dry treatment (DS),water-dispersible powders for slurry treatment (WS), water-solublepowders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels(GF) are usually employed. The compositions in question give, aftertwo-to-tenfold dilution, active substance concentrations of from 0.01 to60% by weight, preferably from 0.1 to 40%, in the ready-to-usepreparations. Application can be carried out before or during sowing.Methods for applying compound I and compositions thereof, respectively,onto plant propagation material, especially seeds, include dressing,coating, pelleting, dusting, and soaking as well as in-furrowapplication methods. Preferably, compound I or the compositions thereof,respectively, are applied on to the plant propagation material by amethod such that germination is not induced, e. g. by seed dressing,pelleting, coating and dusting.

When employed in plant protection, the amounts of active substancesapplied are, depending on the kind of effect desired, from 0.001 to 2 kgper ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e. g. bydusting, coating or drenching seed, amounts of active substance of from0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to100 g and most preferably from 5 to 100 g, per 100 kilogram of plantpropagation material (preferably seeds) are generally required.

When used in the protection of materials or stored products, the amountof active substance applied depends on the kind of application area andon the desired effect. Amounts customarily applied in the protection ofmaterials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of activesubstance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e. g. herbicides, insecticides,fungicides, growth regulators, safeners, biopesticides) may be added tothe active substances or the compositions comprising them as premix or,if appropriate not until immediately prior to use (tank mix). Theseagents can be admixed with the compositions according to the inventionin a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

A pesticide is generally a chemical or biological agent (such aspestidal active ingredient, compound, composition, virus, bacterium,antimicrobial or disinfectant) that through its effect deters,incapacitates, kills or otherwise discourages pests. Target pests caninclude insects, plant pathogens, weeds, mollusks, birds, mammals, fish,nematodes (roundworms), and microbes that destroy property, causenuisance, spread disease or are vectors for disease. The term“pesticide” includes also plant growth regulators that alter theexpected growth, flowering, or reproduction rate of plants; defoliantsthat cause leaves or other foliage to drop from a plant, usually tofacilitate harvest; desiccants that promote drying of living tissues,such as unwanted plant tops; plant activators that activate plantphysiology for defense of against certain pests; safeners that reduceunwanted herbicidal action of pesticides on crop plants; and plantgrowth promoters that affect plant physiology e.g. to increase plantgrowth, biomass, yield or any other quality parameter of the harvestablegoods of a crop plant.

Biopesticides have been defined as a form of pesticides based onmicroorganisms (bacteria, fungi, viruses, nematodes, etc.) or naturalproducts (compounds, such as metabolites, proteins, or extracts frombiological or other natural sources) (U.S. Environmental ProtectionAgency: http://www.epa.gov/pesticides/biopesticides/). Biopesticidesfall into two major classes, microbial and biochemical pesticides:

-   -   (1) Microbial pesticides consist of bacteria, fungi or viruses        (and often include the metabolites that bacteria and fungi        produce). Entomopathogenic nematodes are also classified as        microbial pesticides, even though they are multi-cellular.    -   (2) Biochemical pesticides are naturally occurring substances        that control pests or provide other crop protection uses as        defined below, but are relatively non-toxic to mammals.

The user applies the composition according to the invention usually froma predosage device, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank orany other kind of vessel used for applications (e. g. seed treaterdrums, seed pelleting machinery, knapsack sprayer) and furtherauxiliaries may be added, if appropriate.

When living microorganisms, such as microbial pesticides from groupsL1), L3) and L5), form part of such kit, it must be taken care thatchoice and amounts of the components (e. g. chemical pesticides) and ofthe further auxiliaries should not influence the viability of themicrobial pesticides in the composition mixed by the user. Especiallyfor bactericides and solvents, compatibility with the respectivemicrobial pesticide has to be taken into account.

Consequently, one embodiment of the invention is a kit for preparing ausable pesticidal composition, the kit comprising a) a compositioncomprising component 1) as defined herein and at least one auxiliary;and b) a composition comprising component 2) as defined herein and atleast one auxiliary; and optionally c) a composition comprising at leastone auxiliary and optionally a further active component 3) as definedherein.

Mixing the compounds I or the compositions comprising them in the useform as fungicides with other fungicides results in many cases in anexpansion of the fungicidal spectrum of activity being obtained or in aprevention of fungicide resistance development. Furthermore, in manycases, synergistic effects are obtained.

The following list of pesticides II (e. g. pesticidally-activesubstances and biopesticides), in conjunction with which the compounds Ican be used, is intended to illustrate the possible combinations butdoes not limit them:

A) Respiration Inhibitors

-   -   Inhibitors of complex Ill at Q site: azoxystrobin (A.1.1),        coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin        (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6),        fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8),        kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin        (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13),        pyraclostrobin (A.1.14), pyrametostrobin (A.1.15),        pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17),        2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide        (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb        (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21),        methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)ox-ylmethyl]phenyl]-N-methoxy-carbamate        (A.1.22),        1-[3-chloro-2-[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.23),        1-[3-bromo-2-[[1-(4-chloro-phenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.24),        1-[2-[[1-(4-chloro-phenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one        (A.1.25),        1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one        (A.1.26),        1-[2-[[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one        (A.1.27),        1-[3-cyclopropyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.30),        1-[3-(difluoromethoxy)-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-1-tetrazol-5-one        (A.1.31),        1-methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazol-5-one        (A.1.32),        (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide        (A.1.34),        (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide        (A.1.35), pyriminostrobin (A.1.36), bifujunzhi (A.1.37),        2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic        acid methylester (A.1.38);    -   inhibitors of complex Ill at Q_(i) site: cyazofamid (A.2.1),        amisulbrom (A.2.2),        [(6,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4);    -   inhibitors of complex II: benodanil (A.3.1), benzovindiflupyr        (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5),        fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8),        fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.11),        isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14),        penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen        (A.3.17), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam        (A.3.20), thifluzamide (A.3.21),        3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.22),        3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.23),        1,3-dimethyl-N-(1,1,3-tri-methylindan-4-yl)pyrazole-4-carboxamide        (A.3.24),        3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.25),        1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.26),        3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.27),        3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide        (A.3.28),        N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-5-fluoro-1,3-dimethyl-pyrazole-4-carboxamide        (A.3.29), methyl        (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate        (A.3.30),        N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide        (A.3.31),        2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide        (A.3.32),        2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide        (A.3.33),        2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide        (A.3.34),        2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide        (A.3.35),        2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide        (A.3.36),        2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide        (A.3.37),        2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide        (A.3.38),        2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide        (A.3.39);    -   other respiration inhibitors: diflumetorim (A.4.1); nitrophenyl        derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap        (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone        (A.4.7); organometal compounds: fentin salts, e. g.        fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin        hydroxide (A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12);

B) Sterol Biosynthesis Inhibitors (SBI Fungicides)

-   -   C14 demethylase inhibitors: triazoles: azaconazole (B.1.1),        bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole        (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6),        diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole        (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11),        flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole        (B.1.14), ipconazole (B.1.15), metconazole (B.1.17),        myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole        (B.1.20), penconazole (B.1.21), propiconazole (B.1.22),        prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole        (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27),        triadimenol (B.1.28), triticonazole (B.1.29), uniconazole        (B.1.30), ipfentrifluconazole, (B.1.37), mefentrifluconazole        (B.1.38),        2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol        (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45),        prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines,        pyri-dines and piperazines: fenarimol (B.1.49), pyrifenox        (B.1.50), triforine (B.1.51),        [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol        (B.1.52);    -   Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph        (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4),        tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7),        spiroxamine (B.2.8);    -   Inhibitors of 3-keto reductase: fenhexamid (B.3.1);    -   Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1);

C) Nucleic Acid Synthesis Inhibitors

-   -   phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1),        benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4),        metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);    -   other nucleic acid synthesis inhibitors: hymexazole (C.2.1),        octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4),        5-fluorocytosine (C.2.5),        5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6),        5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7),        5-fluoro-2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);

D) Inhibitors of Cell Division and Cytoskeleton

-   -   tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2),        fuberidazole (D.1.3), thiabendazole (D.1.4), thiophanate-methyl        (D.1.5),        3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine        (D.1.6),        3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine        (D.1.7),        N-eth-yl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide        (D.1.8),        N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide        (D.1.9),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide        (D.1.10),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide        (D.1.11),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide        (D.1.12),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide        (D.1.13),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide        (D.1.14),        2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide        (D.1.15),        4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine        (D.1.16);    -   other cell division inhibitors: diethofencarb (D.2.1), ethaboxam        (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide        (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);

E) Inhibitors of Amino Acid and Protein Synthesis

-   -   methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim        (E.1.2), pyrimethanil (E.1.3);    -   protein synthesis inhibitors: blasticidin-S(E.2.1), kasugamycin        (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin        (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);

F) Signal Transduction Inhibitors

-   -   MAP/histidine kinase inhibitors: fluoroimid (F.1.1), iprodione        (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil        (F.1.5);    -   G protein inhibitors: quinoxyfen (F.2.1);

G) Lipid and Membrane Synthesis Inhibitors

-   -   Phospholipid biosynthesis inhibitors: edifenphos (G.1.1),        iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);    -   lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2),        tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5),        chloroneb (G.2.6), etridiazole (G.2.7);    -   phospholipid biosynthesis and cell wall deposition: dimethomorph        (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph        (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6),        valifenalate (G.3.7);    -   compounds affecting cell membrane permeability and fatty acides:        propamocarb (G.4.1);    -   inhibitors of oxysterol binding protein: oxathiapiprolin        (G.5.1),        2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl        methanesulfonate (G.5.2),        2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)        1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl        methanesulfonate (G.5.3),        4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.4),        4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.5),        4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.6),        4-[1-[2-[5-cyclo-propyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.7),        4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.8),        4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.9),        4-[1-[2-[3,5-bis(trifluoro-methyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.10),        (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide        (G.5.11);        H) Inhibitors with Multi Site Action    -   inorganic active substances: Bordeaux mixture (H.1.1), copper        (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4),        copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur        (H.1.7);    -   thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2),        maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6),        thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);    -   organochlorine compounds: anilazine (H.3.1), chlorothalonil        (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5),        dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene        (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide        (H.3.10), tolylfluanid (H.3.11);    -   guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine        free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5),        iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7),        iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9),        2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone        (H.4.10);

I) Cell Wall Synthesis Inhibitors

-   -   inhibitors of glucan synthesis: validamycin (I.1.1), polyoxin B        (I.1.2);    -   melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole        (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil        (I.2.5);

J) Plant Defence Inducers

-   -   acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil        (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5);        phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7),        phosphorous acid and its salts (J.1.8), calcium phosphonate        (J.1.11), potassium phosphonate (J.1.12), potassium or sodium        bicarbonate (J.1.9),        4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide        (J.1.10);

K) Unknown Mode of Action

-   -   bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3),        cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocymet        (K.1.7), diclomezine (K.1.8), difenzoquat (K.1.9),        difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11),        fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover        (K.1.14), flusulfamide (K.1.15), flutianil (K.1.16), harpin        (K.1.17), methasulfocarb (K.1.18), nitrapyrin (K.1.19),        nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21), oxin-copper        (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24),        tecloftalam (K.1.25), triazoxide (K.1.26),        N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl        formamidine (K.1.27),        N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl        formamidine (K.1.28),        N′-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine        (K.1.29),        N′-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine        (K.1.30),        N′-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine        (K.1.31),        N′-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine        (K.1.32),        N′-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine        (K.1.33),        N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl        formamidine (K.1.34),        N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl        formamidine (K.1.35),        2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide        (K.1.36),        3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine        (pyrisoxazole) (K.1.37),        3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine        (K.1.38),        5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole        (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate        (K.1.40), picarbutrazox (K.1.41), pentyl        N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate        (K.1.42),        but-3-ynylN-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate        (K.1.43),2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]pro-pan-2-ol(K.1.44),2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol        (K.1.45), quinofumelin        (K.1.47),9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine        (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50),        2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline        (K.1.51), dichlobentiazox(K.1.52),        N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine        (K.1.53);

L) Biopesticides

-   -   L1) Microbial pesticides with fungicidal, bactericidal,        viricidal and/or plant defense activator activity: Ampelomyces        quisqualis, Aspergillus flavus, Aureobasidium pullulans,        Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B.        mojavensis, B. mycoides, B. pumilus, B. simplex B. solisalsi B.        subtilis, B. subtilis var. amyloliquefaciens, Candida        oleophila, C. saitoana, Clavibacter        michiganensis(bacteriophages), Coniothyrium minitans,        Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora        alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate        (also named Gliocladium catenulatum), Gliocladium roseum,        Lysobacter antibioticus, L. enzymogenes, Metschnikowia        fructicola, Microdochium dimerum, Microsphaeropsis ochracea,        Muscodor albus, Paenibacillus alvei Paenibacillus polymyxa,        Pantoea vagans, Penicillium bilaiae, Phlebiopsis ggantea,        Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa,        Pichia anomala, Pythium oigandrum, Sphaerodes mycoparasitica,        Streptomyces griseoviridis, S. lydicus, S. violaceusniger        Talaromyces flavus, Trichoderma asperelloides, T. aspereum, T.        atroviride, T. fertile, T. gamsil T. harmatum, T. harzianum, T.        polysporum, T. stromaticum, T. vrens, T. viride, Typhula        phacorrhiza, Ulocladium oudemansi, Verticilium dahlia, zucchini        yellow mosaic virus (avirulent strain);    -   L2) Biochemical pesticides with fungicidal, bactericidal,        viricidal and/or plant defense activator activity: harpin        protein, Reynoutria sachallnensis extract;    -   L3) Microbial pesticides with insecticidal, acaricidal,        molluscidal and/or nematicidal activity: Agrobacterium        radiobacter Bacillus cereus, B. firmus, B. thuringiensis, B.        thuringiensis ssp. aizawai B. t. ssp. israelensis, B. t. ssp.        gaeriae, B. t. ssp. kurstaki B. t. ssp. tenebrionis, Beauveria        bassiana, B. brongniartil Burkholderia spp., Chromobacterium        subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia        leucotreta granulovirus (CrleGV), Flavobacterium spp.,        Hellcoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa        zea nucleopolyhedrovirus (HzNPV), Hellcoverpa zea single capsid        nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora,        Isaria fumosorosea, Lecanicillium longisporum, L. muscarium,        Metarhizium anisopliae, Metarhizium anisopliae var.        anisopliae, M. anisopliae var. acridum, Nomuraea rileyi;        Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus        popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P.        ramosa, P. thornea, P. usgae, Pseudomonas fluorescens,        Spodoptera littoralis nucleopolyhedrovirus (SpliNPV),        Steinernema carpocapsae, S. fetiae, S. kraussei Streptomyces        galbus, S. microflavus;    -   L4) Biochemical pesticides with insecticidal, acaricidal,        molluscidal, pheromone and/or nematicidal activity: L-carvone,        citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate,        (E,Z)-2,4-ethyl decadienoate (pear ester),        (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl        myristate, lavanulyl senecioate, cis-jasmone, 2-methyl        1-butanol, methyl eugenol, methyljasmonate,        (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol        acetate, (E,Z)-3,13-octadecadien-1-ol, R-1-octen-3-ol,        pentatermanone, (E,Z,Z)-3,8,11-tetradecatrienyl acetate,        (Z,E)-9,12-tetradecadien-1-yl acetate, Z-7-tetradecen-2-one,        Z-9-tetradecen-1-yl acetate, Z-11-tetradecenal,        Z-11-tetradecen-1-ol, extract of Chenopodium ambrosiodes, Neem        oil, Quillay extract;    -   L5) Microbial pesticides with plant stress reducing, plant        growth regulator, plant growth promoting and/or yield enhancing        activity: Azospirillum amazonense, A. brasllense, A.        lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium        spp., B. ekanil B. japonicum, B. liaoningense, B. lupini, Deftia        acidovorans, Glomus intraradices, Mesorhzobium spp., Rhizobium        leguminosarum bv. phaseoli R. l. bv. trifoli R. l. bv.        viciae, R. tropic, Sinorhizobium melioti,

M) Growth Regulators

abscisic acid (M.1.1), amidochlor, ancymidol, 6-benzylaminopurine,brassinolide, butralin, chlormequat, chlormequat chloride, cholinechloride, cyclanilide, daminozide, dikegulac, dimethipin,2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet,forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid,maleic hydrazide, mefluidide, mepiquat, mepiquat chloride,naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione,prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol,tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid,trinexapac-ethyl and uniconazole;

N) Herbicides from Classes N.1 to N.15

-   N.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium,    butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim,    cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop,    fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop,    fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop,    haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop,    pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl,    quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl,    quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,    4-(4′-chloro-4-cyclo,    propyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one    (CAS 1312337-72-6);    4-(2′,4′-dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one    (CAS 1312337-45-3);    4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one    (CAS 1033757-93-5);    4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione    (CAS 1312340-84-3);    5-(acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one    (CAS 1312337-48-6);    5-(acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;    5-(acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one    (CAS 1312340-82-1);    5-(acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one    (CAS 1033760-55-2);    4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl    carbonic acid methyl ester (CAS 1312337-51-1);    4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl    carbonic acid methyl ester;    4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl    carbonic acid methyl ester (CAS 1312340-83-2);    4-(2′,4′-dichloro-4-ethyl,[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl    carbonic acid methyl ester (CAS 1033760-58-5); benfuresate,    butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb,    ethofumesate, flupropanate, molinate, orbencarb, pebulate,    prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and    vernolate;-   N.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron,    bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron,    cinosulfuron, cyclosulfamuron, ethametsulfuron,    ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,    flucetosulfuron, flupyrsulfuron, flupyrsulfuronmethyl-sodium,    foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron,    iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron,    iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron,    metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron,    primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron,    pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron,    sulfometuron-methyl, sulfosulfuron, thifensulfuron,    thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,    trifloxysulfuron, triflusulfuron, triflusulfuron-methyl,    tritosulfuron, imazamethabenz, imazamethabenz-methyl, imazamox,    imazapic, imazapyr, imazaquin, imazethapyr; cloransulam,    cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam,    penoxsulam, pyrimisulfan and pyroxsulam; bispyribac,    bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac,    pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium,    4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic    acid-1-methyl¬ethyl ester (CAS 420138-41-6),    4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]¬methyl]amino]-benzoic    acid propyl ester (CAS 420138-40-5),    N-(4-bromo-phenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine    (CAS 420138-01-8); flucarbazone, flucarbazone-sodium,    propoxycarbazone, propoxycarbazone-sodium, thiencarbazone,    thiencarbazone-methyl; triafamone;-   N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine;    ametryn, atrazine, chloridazone, cyanazine, desmetryn,    dimethametryn, hexazinone, metribuzin, prometon, prometryn,    propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn,    trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron,    diuron, fluometuron, isoproturon, isouron, linuron, metamitron,    methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon,    siduron, tebuthiuron, thiadiazuron, desmedipham, karbutilat,    phenmedipham, phenmediphamethyl, bromofenoxim, bromoxynil and its    salts and esters, ioxynil and its salts and esters, bromacil,    lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol,    pentanochlor, propanil; diquat, diquat-dibromide, paraquat,    paraquat-dichloride, paraquat-dimetilsulfate;-   N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen,    acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone,    bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,    chlormethoxyfen, cinidon-ethyl, fluazolate, flufenpyr,    flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin,    fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl,    fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen,    pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl,    saflufenacil, sulfentrazone, thidiazimin, tiafenacil,    trifludimoxazin, ethyl    [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate    (CAS 353292-31-6),    N-ethyl-3-(2,6-dichloro-4-tri-fluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (CAS 452098-92-9), N    tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyl,    phenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N    tetrahydro¬furfuryl-3-(2-chloro-6-fluoro-4-trifluoro¬methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide    (CAS 452100-03-7),    3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione    (CAS 451484-50-7),    2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione    (CAS 1300118-96-0), 1-methyl-6-trifluoro,    methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione    (CAS 1304113-05-0), methyl    (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate    (CAS 948893-00-3),    3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione    (CAS 212754-02-4);-   N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone,    flurochloridone, flurtamone, norflurazon, picolinafen,    4-(3-trifluoromethyl¬phenoxy)-2-(4-trifluoromethylphenyl)¬pyrimidine    (CAS 180608-33-7); benzobicyclon, benzofenap, bicyclopyrone,    clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole,    pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione,    tolpyralate, topramezone; aclonifen, amitrole, flumeturon;-   N.6 EPSP synthase inhibitors: glyphosate,    glyphosate-isopropylammonium, glyposate-potassium,    glyphosate-trimesium (sulfosate);-   N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos),    bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;-   N.8 DHP synthase inhibitors: asulam;-   N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine,    ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine,    trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal,    chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam;    carbetamide, chlorpropham, flamprop, flamprop-isopropyl,    flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;-   N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor,    dimethachlor, dimethenamid, dimethenamid-P, metazachlor,    metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor,    propisochlor, thenylchlor, flufenacet, mefenacet, diphenamid,    naproanilide, napropamide, napropamide-M, fentrazamide, anilofos,    cafenstrole, fenoxasulfone, ipfencarbazone, piperophos,    pyroxasulfone, isoxazoline compounds of the formulae II.1, II.2,    II.3, II.4, II.5, II.6, II.7, II.8 and II.9

-   N.11 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil,    flupoxam, indaziflam, isoxaben, triaziflam,    1-cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine    (CAS 175899-01-1);-   N.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;-   N.13 Auxinic herbicides: 2,4-D and its salts and esters, clacyfos,    2,4-DB and its salts and esters, aminocyclopyrachlor and its salts    and esters, aminopyralid and its salts such as    aminopyralid-dimethylammonium,    aminopyralid-tris(2-hydroxypropyl)ammonium and its esters,    benazolin, benazolin-ethyl, chloramben and its salts and esters,    clomeprop, clopyralid and its salts and esters, dicamba and its    salts and esters, dichlorprop and its salts and esters,    dichlorprop-P and its salts and esters, fluroxypyr,    fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts    and esters (CAS 943832-60-8); MCPA and its salts and esters,    MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its    salts and esters, mecoprop-P and its salts and esters, picloram and    its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its    salts and esters, triclopyr and its salts and esters,    4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)-5-fluoropyridine-2-carboxylic    acid, benzyl    4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate    (CAS 1390661-72-9);-   N.14 Auxin transport inhibitors: diflufenzopyr,    diflufenzopyr-sodium, naptalam and naptalam-sodium;-   N.15 Other herbicides: bromobutide, chlorflurenol,    chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS    499223-49-3) and its salts and esters, dalapon, dazomet,    difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron,    endothal and its salts, etobenzanid, flurenol, flurenol-butyl,    flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic    hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl    azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic    acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine,    tridiphane;    O) Insecticides from Classes 0.1 to 0.29-   O.1 Acetylcholine esterase (AChE) inhibitors: aldicarb, alanycarb,    bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl,    carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate,    furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl,    pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC,    xylylcarb and triazamate; acephate, azamethiphos, azinphos-ethyl,    azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos,    chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos,    cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos,    dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos,    famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,    heptenophos, imicyafos, isofenphos, isopropyl    O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion,    mecarbam, methamidophos, methidathion, mevinphos, monocrotophos,    naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl,    phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,    pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos,    pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos,    terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon,    vamidothion;-   O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane;    ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole;-   O.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans    allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin    S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin,    beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,    cypermethrin, alpha-cypermethrin, beta-cypermethrin,    theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin,    empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate,    flucythrinate, flumethrin, tau-fluvalinate, halfenprox,    heptafluthrin, imiprothrin, meperfluthrin, metofluthrin,    momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin,    pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin,    tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin;    DDT, methoxychlor;-   O.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid,    clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram,    thiacloprid, thiamethoxam;    (2E)-1-[(6-chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide;    1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine;    nicotine;-   O.5 Nicotinic acetylcholine receptor allosteric activators:    spinosad, spinetoram;-   O.6 Chloride channel activators: abamectin, emamectin benzoate,    ivermectin, lepimectin, milbemectin;-   O.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene;    fenoxycarb, pyriproxyfen;-   O.8 miscellaneous non-specific (multi-site) inhibitors: methyl    bromide and other alkyl halides; chloropicrin, sulfuryl fluoride,    borax, tartar emetic;-   O.9 Selective homopteran feeding blockers: pymetrozine, flonicamid;-   O.10 Mite growth inhibitors: clofentezine, hexythiazox,    diflovidazin; etoxazole;-   O.11 Microbial disruptors of insect midgut membranes: Bacillus    thuringiensis, Bacillus sphaericus and the insecticdal proteins they    produce: Bacillus thuringiensis subsp. israelensis, Bacillus    sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus    thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp.    tenebrionis, the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab,    mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1;-   O.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron;    azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;-   O.13 Uncouplers of oxidative phosphorylation via disruption of the    proton gradient: chlorfenapyr, DNOC, sulfluramid;-   O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers:    bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium;-   O.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron,    chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,    hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron,    triflumuron;-   O.16 Inhibitors of the chitin biosynthesis type 1: buprofezin;-   O.17 Moulting disruptors: cyromazine;-   O.18 Ecdyson receptor agonists: methoxyfenozide, tebufenozide,    halofenozide, fufenozide, chromafenozide;-   O.19 Octopamin receptor agonists: amitraz;-   O.20 Mitochondrial complex III electron transport inhibitors:    hydramethylnon, acequinocyl, fluacrypyrim;-   O.21 Mitochondrial complex I electron transport inhibitors:    fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad,    tolfenpyrad; rotenone;-   O.22 Voltage-dependent sodium channel blockers: indoxacarb,    metaflumizone,    2-[2-(4-cyano-phenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide,    N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)-amino]phenyl]methylene]-hydrazinecarboxamide;-   O.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen,    spiromesifen, spirotetramat;-   O.24 Mitochondrial complex IV electron transport inhibitors:    aluminium phosphide, calcium phosphide, phosphine, zinc phosphide,    cyanide;-   O.25 Mitochondrial complex II electron transport inhibitors:    cyenopyrafen, cyflumetofen;-   O.26 Ryanodine receptor-modulators: flubendiamide,    chlorantraniliprole, cyantraniliprole, cyclaniliprole,    tetraniliprole;    (R)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)-ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide,    (S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)-phthalamide,    methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]-carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate;    N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;    N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;    N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;    N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;    N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;    N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide;    3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide;    3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide;    N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide;    cyhalodiamide;-   O.27. insecticidal active compounds of unknown or uncertain mode of    action: afidopyropen, afoxolaner, azadirachtin, amidoflumet,    benzoximate, bifenazate, broflanilide, bromopropylate,    chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim,    flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone,    fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide,    pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen,    triflumezopyrim,    11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one,    3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,    1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine,    Bacillus firmus;    (E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;    (E/Z)—N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;    (E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide;    (E/Z)—N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;    (E/Z)—N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;    (E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;    (E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;    (E/Z)—N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;    (E/Z)—N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide.);    N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide;    N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N′-isopropyl-acetamidine;    fluazaindolizine;    4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide;    fluxametamide;    5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole;    3-(benzoylmethylamino)-N-[2-bromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide;    3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide;    N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;    N-[3-[[[2-bromo-4-[1,2,2,2-tetra-fluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;    4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;    3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;    2-chloro-N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide;    4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoro-methyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;    4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide;    N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;    N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;    N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;    4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;    4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;    N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;    2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine;    2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;    2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;    N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;    N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;    N-ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;    N-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;    N,2-dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;    N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;    N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide;    N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide;    N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methyl-thio-propanamide;    N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide;    1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine;    1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol;    1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;    1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;    N,5-di-methyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide;    1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;    N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;    1-(1,2-di-methylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;    1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;    N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;    1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;    1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide,    N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide;    N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide;    N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide;    2-(3-pyridinyl)-N-(2,2,2-trifluoro-ethyl)-2H-indazole-4-carboxamide;    2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide;    methyl    2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate;    N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide;    N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide;    2-(3-pyridinyl)-N-(2-pyrimidinyl-methyl)-2H-indazole-5-carboxamide;    N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,    N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoro-propylsulfanyl)propanamide;    N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoro-propylsulfinyl)propanamide;    N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide;    N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide;    sarolaner, lotilaner.

The active substances referred to as component 2, their preparation andtheir activity e. g. against harmful fungi is known (cf.:http://www.alanwood.net/pesticides/); these substances are commerciallyavailable. The compounds described by IUPAC nomenclature, theirpreparation and their pesticidal activity are also known (cf. Can. J.Plant Sci. 48(6), 587-94, 1968; EP-A 141317; EP-A 152 031; EP-A 226 917;EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1028125;EP-A1035122; EP-A1201648; EP-A1122 244, JP 2002316902; DE19650197; DE10021412; DE 102005009458; U.S. Pat. Nos. 3,296,272; 3,325,503; WO98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO07/82098; WO 07/90624, WO 10/139271, WO 11/028657, WO 12/168188, WO07/006670, WO 11/77514; WO 13/047749, WO 10/069882, WO 13/047441, WO03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO13/024009, WO 13/24010, WO 13/047441, WO 13/162072, WO 13/092224, WO11/135833, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/116251, WO08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO12/165511, WO 11/081174, WO 13/47441).

The present invention furthermore relates to agrochemical compositionscomprising a mixture of at least one compound I (component 1) and atleast one further active substance useful for plant protection, e. g.selected from the groups A) to O) (component 2), in particular onefurther fungicide, e. g. one or more fungicide from the groups A) to K),as described above, and if desired one suitable solvent or solidcarrier. Those mixtures are of particular interest, since many of themat the same application rate show higher efficiencies against harmfulfungi. Furthermore, combating harmful fungi with a mixture of compoundsI and at least one fungicide from groups A) to K), as described above,is more efficient than combating those fungi with individual compounds Ior individual fungicides from groups A) to K).

By applying compounds I together with at least one active substance fromgroups A) to O) a synergistic effect can be obtained, i.e. more thensimple addition of the individual effects is obtained (synergisticmixtures).

This can be obtained by applying the compounds I and at least onefurther active substance simultaneously, either jointly (e. g. astank-mix) or separately, or in succession, wherein the time intervalbetween the individual applications is selected to ensure that theactive substance applied first still occurs at the site of action in asufficient amount at the time of application of the further activesubstance(s). The order of application is not essential for working ofthe present invention.

When applying compound I and a pesticide II sequentially the timebetween both applications may vary e. g. between 2 hours to 7 days. Alsoa broader range is possible ranging from 0.25 hour to 30 days,preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 daysor from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.In case of a mixture comprising a pesticide II selected from group L),it is preferred that the pesticide II is applied as last treatment.

According to the invention, the solid material (dry matter) of thebiopesticides (with the exception of oils such as Neem oil) areconsidered as active components (e. g. to be obtained after drying orevaporation of the extraction or suspension medium in case of liquidformulations of the microbial pesticides).

In accordance with the present invention, the weight ratios andpercentages used herein for a biological extract such as Quillay extractare based on the total weight of the dry content (solid material) of therespective extract(s).

The total weight ratios of compositions comprising at least onemicrobial pesticide in the form of viable microbial cells includingdormant forms, can be determined using the amount of CFU of therespective microorganism to calculate the total weight of the respectiveactive component with the following equation that 1×10¹⁰ CFU equals onegram of total weight of the respective active component. Colony formingunit is measure of viable microbial cells, in particular fungal 10 andbacterial cells. In addition, here “CFU” may also be understood as thenumber of (juvenile) individual nematodes in case of (entomopathogenic)nematode biopesticides, such as Steinemema feltiae.

In the binary mixtures and compositions according to the invention theweight ratio of the component 1) and the component 2) generally dependsfrom the properties of the active components used, usually it is in therange of from 1:10,000 to 10,000:1, often it is in the range of from1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferablyin the range of from 1:20 to 20:1, more preferably in the range of from1:10 to 10:1, even more preferably in the range of from 1:4 to 4:1 andin particular in the range of from 1:2 to 2:1.

According to further embodiments of the binary mixtures andcompositions, the weight ratio of the component 1) and the component 2)usually is in the range of from 1000:1 to 1:1, often in the range offrom 100:1 to 1:1, regularly in the range of from 50:1 to 1:1,preferably in the range of from 20:1 to 1:1, more preferably in therange of from 10:1 to 1:1, even more preferably in the range of from 4:1to 1:1 and in particular in the range of from 2:1 to 1:1.

According to further embodiments of the mixtures and compositions, theweight ratio of the component 1) and the component 2) usually is in therange of from 20,000:1 to 1:10, often in the range of from 10,000:1 to1:1, regularly in the range of from 5,000:1 to 5:1, preferably in therange of from 5,000:1 to 10:1, more preferably in the range of from2,000:1 to 30:1, even more preferably in the range of from 2,000:1 to100:1 and in particular in the range of from 1,000:1 to 100:1.

According to a further embodiments of the binary mixtures andcompositions, the weight ratio of the component 1) and the component 2)usually is in the range of from 1:1 to 1:1000, often in the range offrom 1:1 to 1:100, regularly in the range of from 1:1 to 1:50,preferably in the range of from 1:1 to 1:20, more preferably in therange of from 1:1 to 1:10, even more preferably in the range of from 1:1to 1:4 and in particular in the range of from 1:1 to 1:2.

According to further embodiments of the mixtures and compositions, theweight ratio of the component 1) and the component 2) usually is in therange of from 10:1 to 1:20,000, often in the range of from 1:1 to1:10,000, regularly in the range of from 1:5 to 1:5,000, preferably inthe range of from 1:10 to 1:5,000, more preferably in the range of from1:30 to 1:2,000, even more preferably in the range of from 1:100 to1:2,000 to and in particular in the range of from 1:100 to 1:1,000.

In the ternary mixtures, i.e. compositions according to the inventioncomprising the component 1) and component 2) and a compound III(component 3), the weight ratio of component 1) and component 2) dependsfrom the properties of the active substances used, usually it is in therange of from 1:100 to 100:1, regularly in the range of from 1:50 to50:1, preferably in the range of from 1:20 to 20:1, more preferably inthe range of from 1:10 to 10:1 and in particular in the range of from1:4 to 4:1, and the weight ratio of component 1) and component 3)usually it is in the range of from 1:100 to 100:1, regularly in therange of from 1:50 to 50:1, preferably in the range of from 1:20 to20:1, more preferably in the range of from 1:10 to 10:1 and inparticular in the range of from 1:4 to 4:1.

Any further active components are, if desired, added in a ratio of from20:1 to 1:20 to the component 1).

These ratios are also suitable for inventive mixtures applied by seedtreatment.

When mixtures comprising microbial pesticides are employed in cropprotection, the application rates preferably range from about 1×10⁶ to5×10¹⁶ (or more) CFU/ha, preferably from about 1×10⁸ to about 1×10¹³CFU/ha, and even more preferably from about 1×10⁹ to 5×10¹⁵ CFU/ha andparticularly preferred even more preferably from 1×10¹² to 5×10¹⁴CFU/ha. In the case of (entomopathogenic) nematodes as microbialpesticides (e. g. Steinernema feltiae), the application rates preferablyrange inform about 1×10⁵ to 1×10¹² (or more), more preferably from 1×10⁸to 1×10¹¹, even more preferably from 5×10⁸ to 1×10¹⁰ individuals (e. g.in the form of eggs, juvenile or any other live stages, preferably in aninfetive juvenile stage) per ha.

When mixtures comprising microbial pesticides are employed in seedtreatment, the application rates with respect to plant propagationmaterial preferably range from about 1×10⁶ to 1×10¹² (or more) CFU/seed.Preferably, the concentration is about 1×10⁶ to about 1×10⁹ CFU/seed. Inthe case of the microbial pesticides II, the application rates withrespect to plant propagation material also preferably range from about1×10⁷ to 1×10¹⁴ (or more) CFU per 100 kg of seed, preferably from 1×10⁹to about 1×10¹² CFU per 100 kg of seed.

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from inhibitors of complex III at Q_(o)site in group A), more preferably selected from compounds (A.1.1),(A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14),(A.1.17), (A.1.21), (A.1.24), (A.1.25), (A.1.26), (A.1.27), (A.1.30),(A.1.31), (A.1.32), (A.1.34) and (A.1.35); particularly selected from(A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17),(A.1.24), (A.1.25), (A.1.26), (A.1.27), (A.1.30), (A.1.31), (A.1.32),(A.1.34) and (A.1.35).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from inhibitors of complex III at Q_(i)site in group A), more preferably selected from compounds (A.2.1),(A.2.3) and (A.2.4); particularly selected from (A.2.3) and (A.2.4).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from inhibitors of complex II in group A),more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4),(A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17),(A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.24),(A.3.25), (A.3.27), (A.3.28), (A.3.29), (A.3.31), (A.3.32), (A.3.33),(A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39);particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9),(A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.24),(A.3.25), (A.3.27), (A.3.29), (A.3.31), (A.3.32), (A.3.33), (A.3.34),(A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from other respiration inhibitors in groupA), more preferably selected from compounds (A.4.5) and (A.4.11); inparticular (A.4.11).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from C14 demethylase inhibitors in groupB), more preferably selected from compounds (B.1.4), (B.1.5), (B.1.8),(B.1.10), (B.1.11), (B.1.12), (B.1.13), (B.1.17), (B.1.18), (B.1.21),(B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.34), (B.1.37),(B.1.38), (B.1.43) and (B.1.46); particularly selected from (B.1.5),(B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33),(B.1.34), (B.1.37), (B.138), (B.1.43) and (B.1.46).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from Delta14-reductase inhibitors in groupB), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6)and (B.2.8); in particular (B.2.4).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from phenylamides and acyl amino acidfungicides in group C), more preferably selected from compounds (C.1.1),(C.1.2), (C.1.4) and (C.1.5); particularly selected from (C.1.1) and(C.1.4).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from other nucleic acid synthesisinhibitors in group C), more preferably selected from compounds (C.2.6),(C.2.7) and (C.2.8).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group D), more preferably selectedfrom compounds (D.1.1), (D.1.2), (D.1.5), (D.2.4) and (D.2.6);particularly selected from (D.1.2), (D.1.5) and (D.2.6).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group E), more preferably selectedfrom compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3); in particular(E.1.3).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group F), more preferably selectedfrom compounds (F.1.2), (F.1.4) and (F.1.5).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group G), more preferably selectedfrom compounds (G.3.1), (G.3.3), (G.3.6), (G.5.1), (G.5.2), (G.5.3),(G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), (G.5.10) and(G.5.11); particularly selected from (G.3.1), (G.5.1), (G.5.2) and(G.5.3).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group H), more preferably selectedfrom compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2),(H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from(H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group I), more preferably selectedfrom compounds (I.2.2) and (I.2.5).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group J), more preferably selectedfrom compounds (J.1.2), (J.1.5), (J.1.8), (J.1.11) and (J.1.12); inparticular (J.1.5).

Preference is also given to mixtures comprising as component 2) at leastone active substance selected from group K), more preferably selectedfrom compounds (K.1.41), (K.1.42), (K.1.44), (K.1.45), (K.1.47) and(K.1.49); particularly selected from (K.1.41), (K.1.44), (K.1.45),(K.1.47) and (K.1.49).

The biopesticides from group L1) and/or L2) may also have insecticidal,acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing,plant growth regulator, plant growth promoting and/or yield enhancingactivity. The biopesticides from group L3) and/or L4) may also havefungicidal, bactericidal, viricidal, plant defense activator, plantstress reducing, plant growth regulator, plant growth promoting and/oryield enhancing activity. The biopesticides from group L5) may also havefungicidal, bactericidal, viricidal, plant defense activator,insecticidal, acaricidal, molluscidal, pheromone and/or nematicidalactivity.

Many of these biopesticides have been deposited under deposition numbersmentioned herein (the prefices such as ATCC or DSM refer to the acronymof the respective culture collection, for details see e. g. here:http://www.wfcc.info/ccinfo/collection/by_acronym/), are referred to inliterature, registered and/or are commercially available: mixtures ofAureobasdium pullulans DSM 14940 and DSM 14941 isolated in 1989 inKonstanz, Germany (e. g. blastospores in Blossom-Protect® from bio-fermGmbH, Austria), Azospirillum brasilense Sp245 originally isolated inwheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR11005; e. g. GELFIX® Gramineas from BASF Agricultural Specialties Ltd.,Brazil), A. brasilense strains Ab-V5 and Ab-V6 (e. g. in AzoMax fromNovozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazilor Simbiose-Maíz® from Simbiose-Agro, Brazil; Plant Soil 331, 413-425,2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 andB-50331; U.S. Pat. No. 8,445,255); B. amyloliquefaciens spp. plantarumD747 isolated from air in Kikugawa-shi, Japan (US 20130236522 A1; FERMBP-8234; e. g. Double Nickel™ 55 WDG from Certis LLC, USA), B.amyloliquefaciens spp. plantarum FZB24 isolated from soil inBrandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot.105, 181-197, 1998; e. g. Taegro® from Novozyme Biologicals, Inc., USA),B. amyloliquefaciens ssp. plantarum FZB42 isolated from soil inBrandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998;e. g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. amyloliquefaciensssp. plantarum MB1600 isolated from faba bean in Sutton Bonington,Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRLB-50595; US 2012/0149571 A1; e. g. Integral® from BASF Corp., USA), B.amyloliquefaciens spp. plantarum QST-713 isolated from peach orchard in1995 in California, U.S.A. (NRRL B-21661; e. g. Serenade® MAX from BayerCrop Science LP, USA), B. amyloliquefaciens spp. plantarum TJ1000isolated in 1992 in South Dakoda, U.S.A. (also called 1BE; ATCC BAA-390;CA 2471555 A1; e. g. QuickRoots™ from TJ Technologies, Watertown, S.Dak., USA), B. firmus CNCM 1-1582, a variant of parental strain EIP-N1(CNCM 1-1556) isolated from soil of central plain area of Israel (WO2009/126473, U.S. Pat. No. 6,406,690; e. g. Votivo® from BayerCropScience LP, USA), B. pumilus GHA 180 isolated from apple treerhizosphere in Mexico (IDAC 260707-01; e. g. PRO-MIX® BX from PremierHorticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to asBU-F22 and BU-F33 isolated at least before 1993 from cucumber infestedby Erwnia trachephila (NRRL B-50185, NRRL B-50153; U.S. Pat. No.8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses inSouth Africa at least before 2008 (NRRL B-50754; WO 2014/029697; e. g.BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., SouthAfrica), B. pumilus QST 2808 was isolated from soil collected inPohnpei, Federated States of Micronesia, in 1998 (NRRL B-30087; e. g.Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU288 (NRRL B-50304; U.S. Pat. No. 8,445,255), B. subtilis FB17 alsocalled UD 1022 or UD10-22 isolated from red beet roots in North America(ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; US2010/0260735; WO 2011/109395); B. thuringiensis ssp. aizawai ABTS-1857isolated from soil taken from a lawn in Ephraim, Wis., U.S.A., in 1987(also called ABG-6346; ATCC SD-1372; e. g. XenTari® from BioFa AG,Munsingen, Germany), B. t. ssp. kurstaki ABTS-351 identical to HD-1isolated in 1967 from diseased Pink Bollworm black larvae inBrownsville, Tex., U.S.A. (ATCC SD-1275; e. g. Dipel® DF from ValentBioSciences, IL, USA), B. t. ssp. kurstaki SB4 isolated from E.saccharina larval cadavers (NRRL B-50753; e. g. Beta Pro® from BASFAgricultural Specialities (Pty) Ltd., South Africa), B. t. ssp.tenebrionis NB-176-1, a mutant of strain NB-125, a wild type strainisolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM5480; EP 585 215 B1; e. g. Novodor® from Valent BioSciences,Switzerland), Beauveria bassiana GHA (ATCC 74250; e. g. BotaniGard®22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g. Naturalis® from CBC (Europe) S.r.l., Italy), B. bassiana PPRI 5339isolated from the larva of the tortoise beetle Conchyloctenia punctata(NRRL 50757; e. g. BroadBand® from BASF Agricultural Specialities (Pty)Ltd., South Africa), Bradyrhizobium elkanii strains SEMIA 5019 (alsocalled 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in1967 in the State of Rio Grande do Sul, from an area previouslyinoculated with a North American isolate, and used in commercialinoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B.japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152;Can. J. Plant. Sci. 70, 661-666, 1990; e. g. in Rhizoflo®, Histick,Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B.japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur.J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011); B.japonicum strains deposited at SEMIA known from Appl. Environ.Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil in Cerradosregion, Brazil by Embrapa-Cerrados used in commercial inoculants since1992 (CPAC 15; e. g. GELFIX 5 or ADHERE 60 from BASF AgriculturalSpecialties Ltd., Brazil), B. japonicum SEMIA 5080 obtained under labconditions by Embrapa-Cerrados in Brazil and used in commercialinoculants since 1992, being a natural variant of SEMIA 586 (CB1809)originally isolated in U.S.A. (CPAC 7; e. g. GELFIX 5 or ADHERE 60 fromBASF Agricultural Specialties Ltd., Brazil); Burkho/der/a sp. A396isolated from soil in Nikko, Japan, in 2008 (NRRL B-50319; WO2013/032693; Marrone Bio Innovations, Inc., USA), Coniothyrium minitansCON/M/91-08 isolated from oilseed rape (WO 1996/021358; DSM 9660; e. g.Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin(alpha-beta) protein (Science 257, 85-88, 1992; e. g. Messenger™ orHARP-N-Tek from Plant Health Care plc, U.K.), Hellcoverpa armigeranucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol. 107, 112-126,2011; e. g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata®from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland,Australia), Hellcoverpa zea single capsid nucleopolyhedrovirus (HzSNPV)(e. g. Gemstar® from Certis LLC, USA), Hellcoverpa zeanucleopolyhedrovirus ABA-NPV-U (e. g. Heligen® from AgBiTech Pty Ltd.,Queensland, Australia), Heterorhabditis bacteriophora (e. g. Nemasys® Gfrom BASF Agricultural Specialities Limited, UK), Isaria fumosoroseaApopka-97 isolated from mealy bug on gynura in Apopka, Fla., U.S.A.(ATCC 20874; Biocontrol Science Technol. 22(7), 747-761, 2012; e. g.PFR-97™ or PreFeRal® from Certis LLC, USA), Metarhizium anisopliae var.anisopliae F52 also called 275 or V275 isolated from codling moth inAustria (DSM 3884, ATCC 90448; e. g. Met52® Novozymes Biologicals BioAgGroup, Canada), Metschnikowia fructicola 277 isolated from grapes in thecentral part of Israel (U.S. Pat. No. 6,994,849; NRRL Y-30752; e. g.formerly Shemer® from Agrogreen, Israel), Paecllomyces ilacinus 251isolated from infected nematode eggs in the Philippines (AGAL 89/030550;WO1991/02051; Crop Protection 27, 352-361, 2008; e. g. BioAct® fromBayer CropScience AG, Germany and MeloCon® from Certis, USA),Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses inSouth Africa at least before 2008 (WO 2014/029697; NRRL B-50755; e.g.BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa),Pasteuria nishizawae Pn1 isolated from a soybean field in the mid-2000sin Illinois, U.S.A. (ATCC SD-5833; Federal Register 76(22), 5808, Feb.2, 2011; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA),Penicillium bilaiae (also called P. bilail) strains ATCC 18309 (=ATCC74319), ATCC 20851 and/or ATCC 22348 (=ATCC 74318) originally isolatedfrom soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J.Plant Sci. 78(1), 91-102, 1998; U.S. Pat. No. 5,026,417, WO 1995/017806;e. g. Jump Start®, Provide® from Novozymes Biologicals BioAg Group,Canada), Reynoutra sachalinenss extract (EP 0307510 B1; e. g. Regalia®SC from Marrone BioInnovations, Davis, Calif., USA or Milsana® fromBioFa AG, Germany), Steinernema carpocapsae (e. g. Millenium® from BASFAgricultural Specialities Limited, UK), S. feltiae (e. g. Nemashield®from BioWorks, Inc., USA; Nemasys® from BASF Agricultural SpecialitiesLimited, UK), Streptomyces microflavus NRRL B-50550 (WO 2014/124369;Bayer CropScience, Germany), Trichoderma asperelloides JM41R isolated inSouth Africa (NRRL 50759; also referred to as T. fertile; e. g.Trichoplus® from BASF Agricultural Specialities (Pty) Ltd., SouthAfrica), T. harzianum T-22 also called KRL-AG2 (ATCC 20847; BioControl57, 687-696, 2012; e. g. Plantshield® from BioWorks Inc., USA or SabrEx™from Advanced Biological Marketing Inc., Van Wert, Ohio, USA).

According to one embodiment of the inventive mixtures, the at least onepesticide II is selected from the groups L1) to L5):

-   L1) Microbial pesticides with fungicidal, bactericidal, viricidal    and/or plant defense activator activity: Aureobasidium pullulans DSM    14940 and DSM 14941 (Li), Bacillus amyloliquefaciens AP-188    (0.1.2), B. amyloliquefaciens ssp. plantarum D747 (L.1.3), B.    amyloliquefaciens ssp. plantarum FZB24 (L.1.4), B. amyloliquefaciens    ssp. plantarum FZB42 (L.1.5), B. amyloliquefaciens ssp. plantarum    MB1600 (L.1.6), B. amyloliquefaciens ssp. plantarum QST-713    (L.1.7), B. amyloliquefaciens ssp. plantarum TJ1000 (L.1.8), B.    pumilus GB34 (L.1.9), B. pumilus GHA 180 (L.1.10), B. pumilus INR-7    (L.1.11), B. pumilus KFP9F (L.1.12), B. pumilus QST 2808    (L.1.13), B. simplex ABU 288 (L.1.14), B. subtilis FB17 (L.1.15),    Coniothyrium minitans CON/M/91-08 (L.1.16), Metschnikowia fructicola    NRRL Y-30752 (L.1.17), Paenibacillus alvei NAS6G6 (L.1.18),    Penicillium bilaiae ATCC 22348 (L.1.19), P. bilaiae ATCC 20851    (L.1.20), Penicillium bilaiae ATCC 18309 (L.1.21), Streptomyces    microflavus NRRL B-50550 (L.1.22), Trichoderma asperelloides JM41R    (L.1.23), T. harzianum T-22 (L.1.24);-   L2) Biochemical pesticides with fungicidal, bactericidal, viricidal    and/or plant defense activator activity: harpin protein (L.2.1),    Reynoutria sachalinensis extract (L.2.2);-   L3) Microbial pesticides with insecticidal, acaricidal, molluscidal    and/or nematicidal activity: Bacillus firmus I-1582 (L.3.1); B.    thuringiensis ssp. aizawai ABTS-1857 (L.3.2), B. t. ssp. kurstaki    ABTS-351 (L.3.3), B. t. ssp. kurstaki SB4 (L.3.4), B. t. ssp.    tenebrionis NB-176-1 (L.3.5), Beauveria bassiana GHA (L.3.6), B.    bassiana JW-1 (L.3.7), B. bassiana PPRI 5339 (L.3.8), Burkho/der/a    sp. A396 (L.3.9), Hellcoverpa armigera nucleopolyhedrovirus    (HearNPV) (L.3.10), Hellcoverpa zea nucleopolyhedrovirus (HzNPV)    ABA-NPV-U (L.3.11), Hellcoverpa zea single capsid    nucleopolyhedrovirus (HzSNPV) (L.3.12), Heterohabditis bacteriophora    (L.3.13), Isaria fumosorosea Apopka-97 (L.3.14), Metarhizium    anisopllae var. anisopllae F52 (L.3.15), Paecllomyces lilacinus 251    (L.3.16), Pasteuria nishizawae Pn1 (L.3.17), Steinernema carpocapsae    (L.3.18), S. feltiae (L.3.19);-   L4) Biochemical pesticides with insecticidal, acaricidal,    molluscidal, pheromone and/or nematicidal activity: cis-jasmone    (L.4.1), methyljasmonate (L.4.2), Quillay extract (L.4.3);-   L5) Microbial pesticides with plant stress reducing, plant growth    regulator, plant growth promoting and/or yield enhancing activity:    Azospirillum brasilense Ab-V5 and Ab-V6 (L.5.1), A. brasilense Sp245    (L.5.2), Bradyrhzobium elkani SEMIA 587 (L.5.3), B. elkani SEMIA    5019 (L.5.4), B. japonicum 532c (L.5.5), B. japoncum E-109    (L.5.6), B. japoncum SEMIA 5079 (L.5.7), B. japonicum SEMIA 5080    (L.5.8).

The present invention furthermore relates to agrochemical compositionscomprising a mixture of XXX (component 1) and at least one biopesticideselected from the group L) (component 2), in particular at least onebiopesticide selected from the groups L1) and L2), as described above,and if desired at least one suitable auxiliary.

The present invention furthermore relates to agrochemical compositionscomprising a mixture of XXX (component 1) and at least one biopesticideselected from the group L) (component 2), in particular at least onebiopesticide selected from the groups L3) and L4), as described above,and if desired at least one suitable auxiliary.

Preference is also given to mixtures comprising as pesticide II(component 2) a biopesticide selected from the groups L1), L3) and L5),preferably selected from strains denoted above as (L1.2), (L.1.3),(L.1.4), (L.1.5), (L1.6), (L.1.7), (L1.8), (L.1.10), (L.1.11), (L.1.12),(L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.19), (L.1.20),(L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2),(L.5.3), (L.5.4), (L.5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2), and(L.4.1); even more preferably selected from (L.1.2), (L.1.6), (L.1.7),(L.1.8), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.18),(L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17),(L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2), and (L.4.1). These mixturesare particularly suitable for treatment of propagation materials, i. e.seed treatment purposes and likewise for soil treatment. These seedtreatment mixtures are particularly suitable for crops such as cereals,corn and leguminous plants such as soybean.

Preference is also given to mixtures comprising as pesticide II(component 2) a biopesticide selected from the groups L1), L3) and L5),preferably selected from strains denoted above as (L.1.22), (L.1.23),(L.1.24), (L.2.2); (L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7),(L.3.8), (L.3.10), (L.3.11), (L.3.12), (L.3.13), (L.3.14), (L.3.15),(L.3.18), (L.3.19); (L.4.2), even more preferably selected from (L.1.2),(L.1.7), (L.1.11), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.23),(L.3.3), (L.3.4), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.11),(L.3.12), (L.3.15), and (L.4.2). These mixtures are particularlysuitable for foliar treatment. These mixtures for foliar treatment areparticularly suitable for vegetables, fruits, vines, cereals, corn,leguminous crops such as soybeans.

The mixtures of active substances can be prepared as compositionscomprising besides the active ingredients at least one inert ingredient(auxiliary) by usual means, e. g. by the means given for thecompositions of compounds I. Concerning usual ingredients of suchcompositions reference is made to the explanations given for thecompositions containing compounds I.

According to one embodiment, the microbial pesticides selected fromgroups L1), L3) and L5) embrace not only the isolated, pure cultures ofthe respective microorganism as defined herein, but also its cell-freeextract, its suspensions in a whole broth culture or as ametabolite-containing culture medium or a purified metabolite obtainedfrom a whole broth culture of the microorganism.

When living microorganisms, such as pesticides II from groups L1), L3)and L5), form part of the compositions, such compositions can beprepared as compositions comprising besides the active ingredients atleast one auxiliary by usual means (e. g. H. D. Burges: Formulation ofMicobial Biopesticides, Springer, 1998). Suitable customary types ofsuch compositions are suspensions, dusts, powders, pastes, granules,pressings, capsules, and mixtures thereof. Examples for compositiontypes are suspensions, capsules, pastes, pastilles, wettable powders ordusts, pressings, granules, insecticidal articles, as well as gelformulations. Herein, it has to be taken into account that eachformulation type or choice of auxiliary should not influence theviability of the microorganism during storage of the composition andwhen finally applied to the soil, plant or plant propagation material.Suitable formulations are e. g. mentioned in WO 2008/002371, U.S. Pat.Nos. 6,955,912, 5,422,107.

SYNTHESIS EXAMPLE

With due modification of the starting compounds, the procedures shown inthe synthesis examples below were used to obtain further compounds I.The resulting compounds, together with physical data, are listed inTable I below.

HPLC-MS: HPLC-column Kinetex XB C18 1.7μ (50×2.1 mm); eluent:acetonitrile/water+0.1% TFA (5 gradient from 5:95 to 100:0 in 1.5 min at60° C., flow gradient from 0.8 to 1.0 ml/min in 1.5 min). MS: QuadrupolElectrospray Ionisation, 80 V (positive mode).

1. Synthesis of2-[2-[(5,6-dimethyl-3-pyridyl)oxy]-6-fluoro-phenyl]-N,2-dimethyl-propanamide(I-1)

To a solution of2-[2-[(5,6-dimethyl-3-pyridyl)oxy]-6-fluoro-phenyl]propan-2-ol (1.07 g,3.9 mmol) in acetic acid (15 mL), acetonitrile (3 mL) and sulfuric acid(3 mL) were added at rt. The reaction was stirred for 2 h at 70° C.,then ice was added and the reaction mixture was quenchend with NaOH topH>10. The aqueous phase was extracted with ethyl acetate, the organicphase was washed with water, dried over Na₂SO₄, concentrated. The crudewas purified via HPLC (water/acetonitrile) to yield 101 mg (8%) of thetitle compound as a colorless oil.

¹H-NMR (CDCl₃, δ in ppm): 8.2 (s, 1H); 7.1 (td, 1H); 7.0 (s, 1H); 6.8(td, 1H); 6.5 (d, 1H); 5.9 (br s, 1H); 2.5 (s, 3H); 2.3 (s, 3H); 1.8 (s,6H); 1.7 (s, 3H),

2. Synthesis of5-[2-(1-benzyloxy-1-methyl-ethyl)-3-fluoro-phenoxy]-2,3-dimethyl-pyrazine(I-3)

¹H-NMR (CDCl₃, δ in ppm): 8.0 (s, 1H); 7.4-7.2 (m, 4H); 7.2 (m, 2H); 7.0(td, 1H); 6.8 (d, 1H); 5.9 (q, 1H); 4.4 (d, 1H), 4.3 (d, 1H), 2.4 (s,3H); 2.3 (s, 3H); 1.6 (d, 3H).

TABLE l

Mp HPLC-MS (R_(t) No. U R4 Q1 Q2 W Q3 [° C.]; [min], M⁺ + H) I-1 CH HCH₃ CH₃ N COCH₃ 0.722 min; M⁺ + H = 317 I-2 N H CH₃ H O CH₂Ph 70 1.329min; M⁺ + H = 353.2 I-3 N CH₃ CH₃ H O CH₂Ph 1.62 min; M⁺ + H = 367.1 I-4N CH₃ CF₃ H O CH₂C₆H₄-4-F 1.405 min; M⁺ + H = 438.39 I-5 CH H CH₃ CH₃ NCOC₆H₄-4-F 0.881 min; M⁺ + H = 397 I-6 CH H CH₃ CH₃ N COC₆H₄-4-Cl 0.918min; M⁺ + H = 413 I-7 CH H CH₃ CH₃ N COCH₂OC₆H₄- 0.932 min; 4-F M⁺ + H =427 I-8 CH H CH₃ CH₃ N COCH₂Cl 0.787 min; M⁺ + H = 351 I-9 CH H CH₃ CH₃N CO(CH₂)₂CH₃ 0.825 min; M⁺ + H = 345.1 I-10 CH H CH₃ CH₃ N CO(CH₂)₄CH₃0.945 min; M⁺ + H = 373.1 I-11 CH H CH₃ CH₃ N CO(CH₂)₃CH₃ 0.896 min;M⁺ + H = 359.0 I-12 CH H CH₃ CH₃ N COCH₂CH₃ 0.789 min; M⁺ + H = 331.2I-13 CH H CH₃ CH₃ N COCH₂- 155 0.665 min; morpholine M⁺ + H = 402.2 I-14N CH₃ CH₃ CH₃ O CH₂Ph 1.381 min; M⁺ + H = 381.1 I-15 N CH₃ CF₃ H OCH(CH₃)C₆H₄- 1.420 min 4-F M⁺ + H = 453.1

II. Biological Trials

Microtest

The active compounds were formulated separately as a stock solutionhaving a concentration of 10000 ppm in dimethyl sulfoxide.

Example 1—Activity Against the Grey Mold Botytis Cinerea in theMicrotiterplate Test

The stock solutions were mixed according to the ratio, pipetted onto amicro titer plate (MTP) and diluted with water to the statedconcentrations. A spore suspension of Botrci cinerea in a DOB mediumsolution was then added. The plates were placed in a watervapor-saturated chamber at a temperature of 18° C. Using an absorptionphotometer, the MTPs were measured at 405 nm 9 days after theinoculation.

In this test, the samples which had been treated with 31 ppm of theactive substance from examples 1-2, I-3, I-5, I-14 and I-15respectively, showed up to at most 6% growth of the pathogen.

Example 2—Activity Against Fusarium culmorum in the Microtiterplate Test

The stock solutions were mixed according to the ratio, pipetted onto amicro titer plate (MTP) and diluted with water to the statedconcentrations. A spore suspension of Fusarium culmorum in an aqueousbiomalt or yeast-bactopeptone-sodiumacetate solution was then added. The15 plates were placed in a water vapor-saturated chamber at atemperature of 18° C. Using an absorption photometer, the MTPs weremeasured at 405 nm 7 days after the inoculation.

In this test, the samples which had been treated with 31 ppm of theactive substance from examples 1-2, I-3, I-14 and I-15 respectively,showed up to at most 17% growth of the pathogen.

Example 3—Activity Against Rice Blast Pyricularia oryzae in theMicrotiterplate Test

The stock solutions were mixed according to the ratio, pipetted onto amicro titer plate (MTP) and diluted with water to the statedconcentrations. A spore suspension of Pyricularia oryzae in a DOB mediumsolution was then added. The plates were placed in a watervapor-saturated chamber at a temperature of 18° C. Using an absorptionphotometer, the MTPs were measured at 405 nm 9 days after theinoculation.

In this test, the samples which had been treated with 31 ppm of theactive substance from examples I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9,I-10, I-11, I-12, I-13, I-14 and I-15 respectively, showed up to at most13% growth of the pathogen.

The measured parameters were compared to the growth of the activecompound-free control variant (100%) and the fungus-free and activecompound-free blank value to determine the relative growth in % of thepathogens in the respective active compounds.

1-15. (canceled)
 16. A compound of formula I

wherein R¹ is in each case independently selected from halogen, OH, NO₂,SH, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C₂-C₄-alkenyl),N(C₂-C₄-alkenyl)₂, NH(C₂-C₄-alkynyl), N(C₂-C₄-alkynyl)₂,NH(C₃-C₆-cycloalkyl), N(C₃-C₆-cycloalkyl)₂,N(C₁-C₄-alkyl)(C₂-C₄-alkenyl), N(C₁-C₄-alkyl)(C₂-C₄-alkynyl),N(C₁-C₄-alkyl)(C₃-C₆-cycloalkyl), N(C₂-C₄-alkenyl)(C₂-C₄-alkynyl),N(C₂-C₄-alkenyl)(C₃-C₆-cycloalkyl), N(C₂-C₄-alkynyl)(C₃-C₆-cycloalkyl),NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x),S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)-aryl, C₁-C₆-cycloalkylthio,S(O)_(m)—C₂-C₆-alkenyl, S(O)_(m)—C₂-C₆-alkynyl, CH(═O),C(═O)C₁-C₆-alkyl, C(═O)C₂-C₆-alkenyl, C(═O)C₂-C₆-alkynyl,C(═O)C₃-C₆-cycloalkyl, C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂,C(═O)N(C₂-C₆-alkenyl)₂, C(═O)N(C₂-C₆-alkynyl)₂,C(═O)N(C₃-C₇-cycloalkyl)₂, CH(═S), C(═S)C₁-C₆-alkyl, C(═S)C₂-C₆-alkenyl,C(═S)C₂-C₆-alkynyl, C(═S)C₃-C₆-cycloalkyl, C(═S)O(C₂-C₆-alkenyl),C(═S)O(C₂-C₆-alkynyl), C(═S)O(C₃-C₇-cycloalkyl), C(═S)NH(C₁-C₆-alkyl),C(═S)NH(C₂-C₆-alkenyl), C(═S)NH(C₂-C₆-alkynyl),C(═S)NH(C₃-C₇-cycloalkyl), C(═S)N(C₁-C₆-alkyl)₂, C(═S)N(C₂-C₆-alkenyl)₂,C(═S)N(C₂-C₆-alkynyl)₂, C(═S)N(C₃-C₇-cycloalkyl)₂, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, OR^(Y),C₃-C₆-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein theheteroaryl contains one, two or three heteroatoms selected from N, O andS; wherein R^(x) is selected from C₁-C₄-alkyl, C₁-C₄-halogenalkyl,unsubstituted aryl or aryl that is substituted by 1, 2, 3, 4 or 5substituents R^(x1) independently selected from C₁-C₄-alkyl, halogen,OH, CN, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy; R^(Y)is selected from C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl,C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl, C₂-C₆-halogenalkynyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, phenyl andphenyl-C₁-C₆-alkyl; wherein the phenyl groups are unsubstituted or carryone, two, three, four or five substituents selected from the groupconsisting of CN, halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy; wherein the acyclic moieties of R¹are unsubstituted or substituted by groups R^(1a) which independently ofone another are selected from: R^(1a) halogen, OH, CN, C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy,C₁-C₆-alkylthio and phenoxy, wherein the phenyl group is unsubstitutedor substituted by substituents R^(11a) selected from the groupconsisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxyand C₁-C₄-halogenalkoxy; wherein the carbocyclic, heteroaryl and arylmoieties of R¹ are unsubstituted or substituted by groups R^(1b) whichindependently of one another are selected from: R^(1b) halogen, OH, CN,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio; andwherein m is 0, 1 and 2; R² is in each case independently selected fromhalogen, OH, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH(C₂-C₄-alkenyl), N(C₂-C₄-alkenyl)₂, NH(C₂-C₄-alkynyl),N(C₂-C₄-alkynyl)₂, NH(C₃-C₆-cycloalkyl), N(C₃-C₆-cycloalkyl)₂,N(C₁-C₄-alkyl)(C₂-C₄-alkenyl), N(C₁-C₄-alkyl)(C₂-C₄-alkynyl),N(C₁-C₄-alkyl)(C₃-C₆-cycloalkyl), N(C₂-C₄-alkenyl)(C₂-C₄-alkynyl),N(C₂-C₄-alkenyl)(C₃-C₆-cycloalkyl), N(C₂-C₄-alkynyl)(C₃-C₆-cycloalkyl),NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x),S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)-aryl, C₁-C₆-cycloalkylthio,S(O)_(m)—C₂-C₆-alkenyl, S(O)_(m)—C₂-C₆-alkynyl, CH(═O),C(═O)C₁-C₆-alkyl, C(═O)C₂-C₆-alkenyl, C(═O)C₂-C₆-alkynyl,C(═O)C₃-C₆-cycloalkyl, C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂,C(═O)N(C₂-C₆-alkenyl)₂, C(═O)N(C₂-C₆-alkynyl)₂,C(═O)N(C₃-C₇-cycloalkyl)₂, CH(═S), C(═S)C₁-C₆-alkyl, C(═S)C₂-C₆-alkenyl,C(═S)C₂-C₆-alkynyl, C(═S)C₃-C₆-cycloalkyl, C(═S)O(C₂-C₆-alkenyl),C(═S)O(C₂-C₆-alkynyl), C(═S)O(C₃-C₇-cycloalkyl), C(═S)NH(C₁-C₆-alkyl),C(═S)NH(C₂-C₆-alkenyl), C(═S)NH(C₂-C₆-alkynyl),C(═S)NH(C₃-C₇-cycloalkyl), C(═S)N(C₁-C₆-alkyl)₂, C(═S)N(C₂-C₆-alkenyl)₂,C(═S)N(C₂-C₆-alkynyl)₂, C(═S)N(C₃-C₇-cycloalkyl)₂, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, OR^(Y),C₃-C₆-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein theheteroaryl contains one, two or three heteroatoms selected from N, O andS; wherein R^(x) is defined as above; R^(Y) is defined as above; whereinthe acyclic moieties of R² are unsubstituted or substituted by groupsR^(2a) which independently of one another are selected from: R^(2a)halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio andphenoxy, wherein the phenyl group is unsubstituted or substituted bysubstituents R^(21a) selected from the group consisting of halogen, OH,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;wherein the carbocyclic, heteroaryl and aryl moieties of R² areunsubstituted or substituted by groups R^(2b) which independently of oneanother are selected from: R^(2b) halogen, OH, CN, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio; and Uis N or CR³; R³ is selected from H, halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, five- orsix-membered heteroaryl and aryl; wherein the heteroaryl contains one,two or three heteroatoms selected from N, O and S; wherein R^(X) isdefined as above; and wherein the aliphatic moieties of R³ areunsubstituted or substituted with identical or different groups R^(3a)which independently of one another are selected from: R^(3a) halogen,OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl and phenoxy, wherein the aryland phenoxy group is unsubstituted or carries 1, 2, 3, 4 or 5substituents R^(31a) selected from the group consisting of halogen, OH,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;and wherein the cycloalkyl, heteroaryl and aryl moieties of R³ areunsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximumnumber of identical or different groups R^(3b) which independently ofone another are selected from: R^(3b) halogen, OH, CN, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio; R⁴ isselected from H, halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, five- or six-memberedheteroaryl and aryl; wherein the heteroaryl contains one, two or threeheteroatoms selected from N, O and S; wherein R^(x) is defined as above;and wherein the aliphatic moieties of R⁴ are unsubstituted orsubstituted with identical or different groups R^(4a) whichindependently of one another are selected from: R^(4a) is selected fromhalogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, aryl andphenoxy, wherein the aryl and phenoxy group is unsubstituted or carries1, 2, 3, 4 or 5 substituents R^(4a) selected from the group consistingof halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy; and wherein the cycloalkyl, heteroaryl and arylmoieties of R⁴ are unsubstituted or substituted with 1, 2, 3, 4, 5 or upto the maximum number of identical or different groups R^(4b) whichindependently of one another are selected from: R^(4b) halogen, OH, CN,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio; Y is Oor S(O)_(m), wherein m is defined as above; Z is N or CR⁵; R⁵ isindependently selected from H, halogen, OH, CN, NO₂, SH, NH₂,NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), CH(═O), C(═O)C₁-C₆-alkyl,C(═O)NH(C₁-C₆-alkyl), CR′═NOR″, C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, S(O)_(m)—C₁-C₆-alkyl, three-, four-, five- orsix-membered saturated or partially unsaturated heterocycle, five- orsix-membered heteroaryl and phenyl; wherein the heterocycle orheteroaryl contains one, two or three heteroatoms selected from N, O andS; and wherein R′ and R″ are independently unsubstituted or substitutedby R′″ which is independently selected from halogen, OH, CN, NO₂, SH,NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl,C₂-C₆-halogenalkynyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl and phenyl; wherein m andR^(x) is as defined above; and wherein the aliphatic moieties of R⁵ arenot further substituted or carry 1, 2, 3 or up to the maximum possiblenumber of identical or different groups R^(5a) which independently ofone another are selected from: R^(5a) halogen, OH, CN, C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, five-or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl,phenyl and phenoxy group is unsubstituted or unsubstituted orsubstituted with R^(51a) selected from the group consisting of halogen,OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy; wherein the alicyclic, phenyl, heterocyclic andheteroaryl moieties of R⁵ are unsubstituted or substituted withidentical or different groups R^(5b) which independently of one anotherare selected from: R^(5b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy, and C₁-C₆-alkylthio; X is independently selectedfrom halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), CH(═O),C(═O)C₁-C₆-alkyl, C(═O)NH(C₁-C₆-alkyl), CR′═NOR″, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₁-C₆-halogenalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, S(O)_(m)—C₁-C₆-alkyl, three-,four-, five- or six-membered saturated or partially unsaturatedheterocycle, five- or six-membered heteroaryl and phenyl; wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; wherein m, R′, R″ and R^(x) is as definedabove; and wherein the aliphatic moieties of X are not furthersubstituted or carry 1, 2, 3 or up to the maximum possible number ofidentical or different groups X^(a) which independently of one anotherare selected from: X^(a) halogen, OH, CN, C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, five-or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl,phenyl and phenoxy group is unsubstituted or unsubstituted orsubstituted with Xia selected from the group consisting of halogen, OH,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;wherein the alicyclic, phenyl, heterocyclic and heteroaryl moieties of Xare unsubstituted or substituted with identical or different groupsX^(b) which independently of one another are selected from: X^(b)halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, andC₁-C₆-alkylthio; n is 0, 1, or 2; Q¹ is selected from CN, halogen,—C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, three-, four-, five- or six-membered saturated orpartially unsaturated heterocycle, five- or six-membered heteroaryl andaryl; wherein the heterocycle and heteroaryl contains one, two or threeheteroatoms selected from N, O and S; wherein the aliphatic moieties ofQ¹ are unsubstituted or substituted with identical or different groupsQ^(1a) which independently of one another are selected from: Q^(1a)halogen, OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, phenyland phenoxy, wherein the phenyl and phenoxy group is unsubstituted orcarries 1, 2, 3, 4 or 5 substituents Q^(1a) selected from the groupconsisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxyand C₁-C₄-halogenalkoxy; wherein the cycloalkyl, heterocyclic,heteroaryl and aryl moieties of Q¹ are unsubstituted or substituted with1, 2, 3, 4, 5 or up to the maximum number of identical or differentgroups Q^(1b) which independently of one another are selected from:Q^(1b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy andC₁-C₆-alkylthio; Q² is selected from H, halogen, —C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,three-, four-, five- or six-membered saturated or partially unsaturatedheterocycle, five- or six-membered heteroaryl and aryl; wherein theheterocycle and heteroaryl contains one, two or three heteroatomsselected from N, O and S; wherein the aliphatic moieties of Q² areunsubstituted or substituted with identical or different groups Q^(2a)which independently of one another are selected from: Q^(2a) halogen,OH, CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, phenyl and phenoxy, wherein thephenyl and phenoxy group is unsubstituted or substituted with 1, 2, 3, 4or 5 substituents Q¹² selected from the group consisting of halogen, OH,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;wherein the cycloalkyl, heterocyclic, heteroaryl and aryl moieties of Q²are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximumnumber of identical or different groups Q^(2b) which independently ofone another are selected from: Q^(2b) halogen, OH, CN, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio;wherein Q¹ and Q² together with the carbon atom to which they are boundform a three- to seven-membered saturated or partially unsaturatedcarbo-, or heterocycle; wherein the ring may further contain 1, 2, 3 or4 heteroatoms selected from N—R^(N), O and S, wherein R^(N) is selectedfrom H, C₁-C₄-alkyl and SO₂R^(Q); wherein R^(Q) is selected fromC₁-C₄-alkyl, C₁-C₄-halogenalkyl, unsubstituted aryl or heteroaryl thatis substituted by 1, 2, 3, 4 or 5 substituents R^(Q1) independentlyselected from C₁-C₄-alkyl; and wherein S may be in the form of its oxideSO or SO₂; and wherein in each case one or two CH₂ groups of the carbo-or heterocycle may be replaced by a group independently selected fromC(═O) and C(═S); and wherein the ring is unsubstituted or substitutedwith 1, 2, 3, 4, 5 or up to the maximum number of identical or differentgroups R^(QR) which independently of one another are selected from:R^(QR) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy andC₁-C₆-alkylthio; W is O, S(O)_(m) or NQ⁴ m is defined as above; Q³ isselected from substituted C₁-C₁₅-alkyl, C₁-C₁₅-halogenalkyl,C₂-C₁₅-alkenyl, C₂-C₁₅-halogenalkenyl, C₂-C₁₅-alkynyl, C₃-C₇-cycloalkyl,S(O)_(m)—C₁-C₁₅-alkyl, S(O)_(m)—C₁-C₁₅-alkoxy, S(O)_(m)-aryl,S(O)_(m)—C₂-C₁₅-alkenyl, S(O)_(m)—C₂-C₁₅-alkynylC(═O)C₁-C₁₅-alkyl,C(═O)C₁-C₁₅-halogenalkyl, C(═O)C₂-C₁₅-alkenyl, C(═O)C₂-C₁₅-alkynyl,C(═O)C₃-C₇-cycloalkyl, C(═O)aryl, C(═O)NH(C₁-C₁₅-alkyl),C(═O)N(C₁-C₁₅-alkyl)₂, C(═O)NH(C₂-C₁₅-alkenyl), C(═O)N(₂—C₁₅-alkenyl)₂,C(═O)NH(C₂-C₁₅-alkynyl), C(═O)N(C₂-C₁₅-alkynyl)₂,C(═O)NH(C₃-C₇-cycloalkyl), C(═O)N(C₃-C₇-cycloalkyl)₂C(═S)C₁-C₁₅-alkyl,C(═S)C₂-C₁₅-alkenyl, C(═S)C₂-C₁₅-alkynyl, C(═S)C₃-C₆-cycloalkyl,C(═S)aryl, C(═S)O(C₁-C₁₅-alkyl), C(═S)O(C₂-C₁₅-alkenyl),C(═S)O(C₂-C₁₅-alkynyl), C(═S)O(C₃-C₇-cycloalkyl), C(═S)NH(C₁-C₁₅-alkyl),C(═S)NH(C₂-C₁₅-alkenyl), C(═S)NH(C₂-C₁₅-alkynyl),C(═S)NH(C₃-C₇-cycloalkyl), C(═S)N(C₁-C₁₅-alkyl)₂,C(═S)N(C₂-C₁₅-alkenyl)₂, C(═S)N(C₂-C₁₅-alkynyl)₂,C(═S)N(C₃-C₇-cycloalkyl)₂, C₃-C₆-cycloalkyl, three-, four-, five- orsix-membered saturated or partially unsaturated heterocycle, five- orsix-membered heteroaryl, and aryl; wherein the heterocycle andheteroaryl contains one, two or three heteroatoms selected from N, O andS; wherein in each case one or two CH₂ groups of the carbocycle andheterocycle may be replaced by a group independently selected from C(═O)and C(═S) wherein the aliphatic moieties of Q³ except for substitutedC₁-C₁₅-alkyl moieties are unsubstituted or substituted with identical ordifferent groups Q^(3a) which independently of one another are selectedfrom: Q^(3a) halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-halogenalkylthio, S(O)_(m)—C₁-C₆-alkyl,S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl, CH(═O), C(═O)C₁-C₆-alkyl,C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl), C(═O)N(C₁-C₆-alkyl)₂,CR′═NOR″, C₁-C₆-alkoxy C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, phenyl, phenoxy and five- toten-membered heterocycle, heteroaryl, heterocycloxy and heteryloxy;wherein in each case one or two CH₂ groups of the carbocycle andheterocycle may be replaced by a group independently selected from C(═O)and C(═S); wherein the heterocycle or heteroaryl contains one, two orthree heteroatoms selected from N, O and S; wherein the carbocyclic,heterocyclic, aryl, phenoxy, and heteroaryl groups are unsubstituted orsubstituted with 1, 2, 3, 4 or 5 substituents Q^(31a) selected from thegroup consisting of halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂,NH—SO₂—R^(x), C₁-C₆-alkylthio, S(O)_(m)—C₁-C₆-alkyl, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, CR′═NOR″, phenyl,phenoxy and five- to ten-membered heterocycle and heteroaryl; whereinthe heterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; and wherein the phenyl, phenoxy, heterocycleand heteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4or 5 substituents Q^(311a) selected from the group consisting ofhalogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, CN, CR′═NOR″and C₁-C₄-halogenalkoxy; and wherein m, R, R′ and R″ is defined asabove; wherein the carbocycle, heterocycle, heteroaryl and aryl moietiesof Q³ are unsubstituted or substituted with 1, 2, 3, 4, 5 or up to themaximum number of identical or different groups Q^(3b) whichindependently of one another are selected from: Q^(3b) halogen, OH, CN,NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₄-alkyl, C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy,C₁-C₆-alkylthio, S(O)_(m)—C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl,phenoxy and five- to ten-membered heterocycle, heteroaryl,heterocycloxy, heteryloxy; wherein the heterocycle or heteroarylcontains one, two or three heteroatoms selected from N, O and S; whereinthe phenyl, phenoxy, heterocycle and heteroaryl groups are unsubstitutedor substituted with 1, 2, 3, 4 or 5 substituents Q^(31b) selected fromthe group consisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, CR′═NOR″; phenyl, phenoxy and five-to ten-membered heterocycle and heteroaryl; wherein the heterocycle orheteroaryl contains one, two or three heteroatoms selected from N, O andS; and wherein the phenyl, phenoxy, heterocycle and heteroaryl groupsare unsubstituted or substituted with 1, 2, 3, 4 or 5 substituentsQ^(311b) selected from the group consisting of halogen, OH, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, CN, CR′═NOR″ and C₁-C₄-halogenalkoxy;and wherein R′ and R″ are defined as above; wherein the substitutedC₁-C₁₅-alkyl moieties of Q³ carry one, two, three or up to the maximumpossible number of identical or different groups Q³, respectively, whichindependently of one another are selected from: Q^(3c) halogen, OH, CN,NO₂, SH, NH₂, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl),N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,C₃-C₆-halogencycloalkyl, C₁-C₆-alkylthio, C₁-C₆-halogenalkylthio,S(O)_(m)—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)-aryl,CH(═O), C(═O)C₁-C₆-alkyl, C(═O)O(C₁-C₆-alkyl), C(═O)NH(C₁-C₆-alkyl),C(═O)N(C₁-C₆-alkyl)₂, CR′═NOR″, a saturated or partially unsaturatedthree-, four-, five-, six-, seven-, eight-, nine-, or ten-memberedcarbocycle or heterocycle, aryl and five-, six- or ten-memberedheteroaryl, heterocycloxy, heteryloxy; wherein in each case one or twoCH₂ groups of the carbocycle and heterocycle may be replaced by a groupindependently selected from C(═O) and C(═S); wherein the heterocycle andheteroaryl contain independently one, two, three or four heteroatomsselected from N, O and S; wherein the carbocyclic, heterocyclic, aryl,phenoxy and heteroaryl groups are independently unsubstituted or carryone, two, three, four or five substituents Q^(31c) selected from thegroup consisting of halogen, OH, CN, NO₂, SH, NH₂, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH(C(═O)C₁-C₄-alkyl), N(C(═O)C₁-C₄-alkyl)₂, NH—SO₂—R,C₁-C₆-alkylthio, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy,C₁-C₄-halogenalkoxy, S(O)_(m)—C₁-C₆-alkyl and CR′═NOR″; phenyl, phenoxyand five- to ten-membered heterocycle and heteroaryl; wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; and wherein the phenyl, phenoxy, heterocycleand heteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4or 5 substituents Q^(311c) selected from the group consisting ofhalogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, CN, CR′═NOR″and C₁-C₄-halogenalkoxy; and wherein R′ and R″ is defined as above;wherein m, R, R′ and R″ is as defined above; Q⁴ is selected fromhydrogen, OH, CH(═O), C(═O)C₁-C₆-alkyl, C(═O)C₂-C₆-alkenyl,C(═O)C₂-C₆-alkynyl, C(═O)C₃-C₆-cycloalkyl, C(═O)O(C₁-C₆-alkyl),C(═O)O(C₂-C₆-alkenyl), C(═O)O(C₂-C₆-alkynyl), C(═O)O(C₃-C₆-cycloalkyl),C(═O)NH(C₁-C₆-alkyl), C(═O)NH(C₂-C₆-alkenyl), C(═O)NH(C₂-C₆-alkynyl),C(═O)NH(C₃-C₆-cycloalkyl), C(═O)N(C₁-C₆-alkyl)₂, C(═O)N(C₂-C₆-alkenyl)₂,C(═O)N(C₂-C₆-alkynyl)₂, C(═O)N(C₃-C₆-cycloalkyl)₂, CH(═S),C(═S)C₁-C₆-alkyl, C(═S)C₂-C₆-alkenyl, C(═S)C₂-C₆-alkynyl,C(═S)C₃-C₆-cycloalkyl, C(═S)O(C₁-C₆-alkyl), C(═S)O(C₂-C₆-alkenyl),C(═S)O(C₂-C₆-alkynyl), C(═S)O(C₃-C₆-cycloalkyl), C(═S)NH(C₁-C₆-alkyl),C(═S)NH(C₂-C₆-alkenyl), C(═S)NH(C₂-C₆-alkynyl),C(═S)NH(C₃-C₆-cycloalkyl), C(═S)N(C₁-C₆-alkyl)₂, C(═S)N(C₂-C₆-alkenyl)₂,C(═S)N(C₂-C₆-alkynyl)₂, C(═S)N(C₃-C₆-cycloalkyl)₂, C₁-C₆-alkyl,C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, OR^(Y), C₁-C₆-alkylthio,C₁-C₆-halogenalkylthio, C₂-C₆-alkenyl, C₂-C₆-halogenalkenylC₂-C₆-alkynyl, C₂-C₆-halogenalkynyl, S(O)_(m)—C₁-C₆-alkyl,S(O)_(m)—C₁-C₆-halogenalkyl, S(O)_(m)—C₁-C₆-alkoxy,S(O)_(m)—C₂-C₆-alkenyl, S(O)_(m)—C₂-C₆-alkynyl, S(O)_(m)aryl,SO₂—NH(C₁-C₆-alkyl), SO₂—NH(C₁-C₆-halogenalkyl), SO₂—NH-aryl, tri-(C₁-C₆alkyl)silyl and di-(C₁-C₆ alkoxy)phosphoryl), five- or six-memberedheteroaryl and aryl; wherein the heteroaryl contains one, two or threeheteroatoms selected from N, O and S; wherein the aryl groups areunsubstituted or carry one, two, three, four or five substituentsselected from the group consisting of CN, halogen, OH, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy; R^(Y) isdefined as above; wherein the acyclic moieties of Q⁴ are not furthersubstituted or carry one, two, three or up to the maximum possiblenumber of identical or different groups Q^(4a) which independently ofone another are selected from: Q^(4a) halogen, OH, CN, C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C₃-C₆-halogencycloalkyl,C₃-C₆-halogencycloalkenyl, C₁-C₄-halogenalkoxy, C₁-C₆-alkylthio, five-or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl,phenyl and phenoxy group is unsubstituted or carries one, two, three,four or five substituents Q^(4a′) selected from the group consisting ofhalogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy andC₁-C₄-halogenalkoxy; wherein the alicyclic, phenyl, heterocyclic andheteroaryl moieties of Q⁴ are not further substituted or carry one, two,three, four, five or up to the maximum number of identical or differentgroups Q^(4b) which independently of one another are selected from:Q^(4b) halogen, OH, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy andC₁-C₆-alkylthio; and wherein m is defined as above; with the provisothat if U is CR³ W cannot be O or S(O)_(m) and of an agriculturallyacceptable salt thereof. and of the compositions for combatingphytopathogenic fungi.
 17. The compound of claim 16, wherein R¹ and R²are selected from halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,OR^(Y) or C₃-C₆-cycloalkyl, wherein the aliphatic moieties of R¹ or R²are unsubstituted or substituted with identical or different groupsR^(1a) or R^(2a) which independently of one another are selected from:R^(1a), R^(2a) halogen, phenyl and phenoxy, wherein the phenyl andphenoxy group is unsubstituted or carries 1, 2, 3, 4 or 5 substituentsR^(11a) or R^(21a) selected from the group consisting of halogen, OH,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;and wherein the cycloalkyl, heteroaryl and aryl moieties of R¹ or R² areunsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximumnumber of identical or different groups R^(1b) or R^(2b) whichindependently of one another are selected from: R^(1b), R^(2b) ishalogen. wherein, R^(Y) is C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl, C₂-C₆-halogenalkenyl, C₂-C₆-alkynyl,C₂-C₆-halogenalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl, phenylor phenyl-C₁-C₆-alkyl.
 18. The compound of claim 16, wherein R⁴ isselected from hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkoxy, and C₃-C₆-cycloalkyl, wherein the aliphaticmoieties of R⁴ are unsubstituted or substituted with identical ordifferent groups R^(4a) which independently of one another are selectedfrom: R^(4a) halogen, phenyl and phenoxy, wherein the phenyl and phenoxygroup is unsubstituted or carries 1, 2, 3, 4 or 5 substituents R^(41a)selected from the group consisting of halogen, OH, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy; and whereinthe cycloalkyl, heteroaryl and aryl moieties of R⁴ are unsubstituted orsubstituted with 1, 2, 3, 4, 5 or up to the maximum number of identicalor different groups R^(4b) which independently of one another areselected from: R^(4b) halogen.
 19. The compound of claim 16, wherein Yis O.
 20. The compound of claim 16, wherein Y is S(O)₂.
 21. The compoundof claim 16, wherein Q¹ is in each case independently selected fromhalogen, C₁-C₆-alkyl, C₁-C₆-halogenalkyl or C₂-C₆-alkenyl; and Q² is ineach case independently selected from H, halogen, C₁-C₆-alkyl,C₁-C₆-halogenalkyl or C₂-C₆-alkenyl; and Q¹ and Q² together with thecarbon atom to which they are bound form a three- to seven-memberedsaturated carbo- or heterocycle, wherein the ring may further contain 1,2, 3 or 4 heteroatoms selected from O and wherein in each case one ortwo CH₂ groups of the carbo- or heterocycle may be replaced by a groupindependently selected from C(═O) and C(═S); and wherein the ring isunsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximumnumber of identical or different groups R^(QR) which independently ofone another are selected from: Q^(R) halogen, OH, CN, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio. 22.The compound of claim 16, wherein Q³ is in each case independentlyselected from substituted C₁-C₁₅-alkyl, C₁-C₁₅-halogenalkyl,C₂-C₁₅-alkenyl, C₂-C₁₅-halogenalkenyl, C₂-C₁₅-alkynyl, C₃-C₇-cycloalkyl,S(O)₂—C₁-C₁₅-alkyl, S(O)₂-aryl, S(O)—C₂-C₁₅-alkenyl,S(O)₂—C₂-C₁₅-alkynyl, C(═O)C₁-C₁₅-alkyl, C(═O)C₁-C₁₅-halogenalkyl,C(═O)C₂-C₁₅-alkenyl, C(═O)C₂-C₁₅-alkynyl, C(═O)C₃-C₇-cycloalkyl,C(═O)aryl, C₃-C₆-cycloalkyl, three-, four-, five- or six-memberedsaturated or partially unsaturated heterocycle, five- or six-memberedheteroaryl, and aryl; wherein the aliphatic moieties of Q³ except forsubstituted C₁-C₁₅-alkyl moieties are unsubstituted or substituted withidentical or different groups Q^(3a) which independently of one anotherare selected from: Q^(3a) halogen, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NNH—SO₂—R^(x), S(O)₂—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl,S(O)₂-aryl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy, phenyl, phenoxy and five- to ten-memberedheterocycle, heteroaryl, heterocycloxy, heteryloxy; wherein in each caseone or two CH₂ groups of the carbocycle and heterocycle may be replacedby a group independently selected from C(═O) and C(═S); wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; wherein the phenyl, phenoxy, heterocycle andheteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5substituents Q^(31a) selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the phenyl, phenoxy,heterocycle and heteroaryl groups are unsubstituted or substituted with1, 2, 3, 4 or 5 substituents Q^(311a) selected from the group consistingof halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, orC₁-C₄-halogenalkoxy; wherein the carbocycle, heterocycle, heteroaryl andaryl moieties of Q³ are unsubstituted or substituted with 1, 2, 3, 4, 5or up to the maximum number of identical or different groups Q^(3b)which independently of one another are selected from: Q^(3b) halogen,CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy, phenyl, phenoxy and five- to ten-memberedheterocycle, heteroaryl, heterocycloxy, heteryloxy; wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; wherein the phenyl, phenoxy, heterocycle andheteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5substituents Q^(31b) selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the phenyl, phenoxy,heterocycle and heteroaryl groups are unsubstituted or substituted with1, 2, 3, 4 or 5 substituents Q^(311b) selected from the group consistingof halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, orC₁-C₄-halogenalkoxy; wherein the substituted C₁-C₁₅-alkyl moieties of Q³carry one, two, three or up to the maximum possible number of identicalor different groups Q³, respectively, which independently of one anotherare selected from: Q^(3c) halogen, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₃-C₆-halogencycloalkyl,S(O)₂—C₁-C₆-alkyl, S(O)₂—C₁-C₆-halogenalkyl, S(O)₂-aryl, a saturated orpartially unsaturated three-, four-, five-, six-, seven-, eight-, nine-,or ten-membered carbocycle or heterocycle, aryl and five-, six- orten-membered heteroaryl, heterocycloxy, heteryloxy; wherein in each caseone or two CH₂ groups of the carbocycle and heterocycle may be replacedby a group independently selected from C(═O) and C(═S); wherein theheterocycle and heteroaryl contain independently one, two, three or fourheteroatoms selected from N, O and S; wherein the carbocyclic,heterocyclic, aryl, phenoxy and heteroaryl groups are independentlyunsubstituted or carry one, two, three, four or five substituentsQ^(31c) selected from the group consisting of halogen, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, S(O)₂—C₁-C₆-alkyl; phenyl, phenoxyand five- to ten-membered heterocycle and heteroaryl; wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; and wherein the phenyl, phenoxy, heterocycleand heteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4or 5 substituents Q^(311c) selected from the group consisting ofhalogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, andC₁-C₄-halogenalkoxy.
 23. The compound of claim 16, wherein U is N and Wis O.
 24. The compound of claim 16, wherein U is N and W is NQ⁴.
 25. Thecompound of claim 16, wherein U is CR³ and W is NQ⁴, wherein R³ is ineach case independently selected from H, halogen, C₁-C₆-alkyl,C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₃-C₆-cycloalkyl, wherein the aliphatic moieties of R³ are unsubstitutedor substituted with identical or different groups R^(3a) whichindependently of one another are selected from: R^(3a) halogen, phenyland phenoxy, wherein the phenyl and phenoxy group is unsubstituted orcarries 1, 2, 3, 4 or 5 substituents R^(31a) selected from the groupconsisting of halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxyand C₁-C₄-halogenalkoxy; and wherein the cycloalkyl, heteroaryl and arylmoieties of R³ are unsubstituted or substituted with 1, 2, 3, 4, 5 or upto the maximum number of identical or different groups R^(3b) whichindependently of one another are selected from: R^(3b) halogen.
 26. Thecompound of claim 16, wherein Q⁴ is in each case independently selectedfrom hydrogen, C(═O)C₁-C₆-alkyl, C(═O)OC₁-C₆-alkyl, C(═O)NHC₁-C₆-alkyl,S(O)₂—C₁-C₆-alkyl, S(O)₂-aryl, SO₂—NH(C₁-C₆-alkyl), OR^(Y), orC₁-C₄-alkyl, wherein R^(Y) is C₁-C₆-alkyl, C₁-C₆-halogenalkyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl.
 27. A composition comprising onecompound of claim 16, an N-oxide or an agriculturally acceptable saltthereof.
 28. A method for combating phytopathogenic fungi, comprisingtreating the fungi or the materials, plants, the soil or seeds to beprotected against fungal attack with an effective amount of at least onecompound of claim
 16. 29. A seed coated with at least one compound ofclaim 16 or an agriculturally acceptable salt thereof, in an amount offrom 0.1 to 10 kg per 100 kg of seed.
 30. The compound of claim 17,wherein R⁴ is selected from hydrogen, halogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, and C₃-C₆-cycloalkyl,wherein the aliphatic moieties of R⁴ are unsubstituted or substitutedwith identical or different groups R^(4a) which independently of oneanother are selected from: R^(4a) halogen, phenyl and phenoxy, whereinthe phenyl and phenoxy group is unsubstituted or carries 1, 2, 3, 4 or 5substituents R^(41a) selected from the group consisting of halogen, OH,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy and C₁-C₄-halogenalkoxy;and wherein the cycloalkyl, heteroaryl and aryl moieties of R⁴ areunsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximumnumber of identical or different groups R^(4b) which independently ofone another are selected from: R^(4b) halogen.
 31. The compound of claim17, wherein Y is O.
 32. The compound of claim 17, wherein Q¹ is in eachcase independently selected from halogen, C₁-C₆-alkyl,C₁-C₆-halogenalkyl or C₂-C₆-alkenyl; and Q² is in each caseindependently selected from H, halogen, C₁-C₆-alkyl, C₁-C₆-halogenalkylor C₂-C₆-alkenyl; and Q¹ and Q² together with the carbon atom to whichthey are bound form a three- to seven-membered saturated carbo- orheterocycle, wherein the ring may further contain 1, 2, 3 or 4heteroatoms selected from 0 and wherein in each case one or two CH₂groups of the carbo- or heterocycle may be replaced by a groupindependently selected from C(═O) and C(═S); and wherein the ring isunsubstituted or substituted with 1, 2, 3, 4, 5 or up to the maximumnumber of identical or different groups R^(QR) which independently ofone another are selected from: Q^(R) halogen, OH, CN, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halogencycloalkyl, C₁-C₄-halogenalkoxy and C₁-C₆-alkylthio. 33.The compound of claim 17, wherein Q³ is in each case independentlyselected from substituted C₁-C₁₅-alkyl, C₁-C₁₅-halogenalkyl,C₂-C₁₅-alkenyl, C₂-C₁₅-halogenalkenyl, C₂-C₁₅-alkynyl, C₃-C₇-cycloalkyl,S(O)₂—C₁-C₁₅-alkyl, S(O)₂-aryl, S(O)—C₂-C₁₅-alkenyl,S(O)₂—C₂-C₁₅-alkynyl, C(═O)C₁-C₁₅-alkyl, C(═O)C₁-C₁₅-halogenalkyl,C(═O)C₂-C₁₅-alkenyl, C(═O)C₂-C₁₅-alkynyl, C(═O)C₃-C₇-cycloalkyl,C(═O)aryl, C₃-C₆-cycloalkyl, three-, four-, five- or six-memberedsaturated or partially unsaturated heterocycle, five- or six-memberedheteroaryl, and aryl; wherein the aliphatic moieties of Q³ except forsubstituted C₁-C₁₅-alkyl moieties are unsubstituted or substituted withidentical or different groups Q^(3a) which independently of one anotherare selected from: Q^(3a) halogen, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂, NNH—SO₂—R^(x), S(O)₂—C₁-C₆-alkyl, S(O)_(m)—C₁-C₆-halogenalkyl,S(O)₂-aryl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy, phenyl, phenoxy and five- to ten-memberedheterocycle, heteroaryl, heterocycloxy, heteryloxy; wherein in each caseone or two CH₂ groups of the carbocycle and heterocycle may be replacedby a group independently selected from C(═O) and C(═S); wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; wherein the phenyl, phenoxy, heterocycle andheteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5substituents Q^(3a) selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the phenyl, phenoxy,heterocycle and heteroaryl groups are unsubstituted or substituted with1, 2, 3, 4 or 5 substituents Q^(311a) selected from the group consistingof halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, orC₁-C₄-halogenalkoxy; wherein the carbocycle, heterocycle, heteroaryl andaryl moieties of Q³ are unsubstituted or substituted with 1, 2, 3, 4, 5or up to the maximum number of identical or different groups Q^(3b)which independently of one another are selected from: Q^(3b) halogen,CN, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogencycloalkyl,C₁-C₄-halogenalkoxy, phenyl, phenoxy and five- to ten-memberedheterocycle, heteroaryl, heterocycloxy, heteryloxy; wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; wherein the phenyl, phenoxy, heterocycle andheteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4 or 5substituents Q^(31b) selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy,phenyl, phenoxy and five- to ten-membered heterocycle and heteroaryl;wherein the heterocycle or heteroaryl contains one, two or threeheteroatoms selected from N, O and S; and wherein the phenyl, phenoxy,heterocycle and heteroaryl groups are unsubstituted or substituted with1, 2, 3, 4 or 5 substituents Q^(311b) selected from the group consistingof halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, orC₁-C₄-halogenalkoxy; wherein the substituted C₁-C₁₅-alkyl moieties of Q³carry one, two, three or up to the maximum possible number of identicalor different groups Q³, respectively, which independently of one anotherare selected from: Q^(3c) halogen, NH(C₁-C₄-alkyl), N(C₁-C₄-alkyl)₂,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₃-C₆-halogencycloalkyl,S(O)₂—C₁-C₆-alkyl, S(O)₂—C₁-C₆-halogenalkyl, S(O)₂-aryl, a saturated orpartially unsaturated three-, four-, five-, six-, seven-, eight-, nine-,or ten-membered carbocycle or heterocycle, aryl and five-, six- orten-membered heteroaryl, heterocycloxy, heteryloxy; wherein in each caseone or two CH₂ groups of the carbocycle and heterocycle may be replacedby a group independently selected from C(═O) and C(═S); wherein theheterocycle and heteroaryl contain independently one, two, three or fourheteroatoms selected from N, O and S; wherein the carbocyclic,heterocyclic, aryl, phenoxy and heteroaryl groups are independentlyunsubstituted or carry one, two, three, four or five substituentsQ^(31c) selected from the group consisting of halogen, NH(C₁-C₄-alkyl),N(C₁-C₄-alkyl)₂, NH—SO₂—R^(x), C₁-C₄-alkyl, C₁-C₄-halogenalkyl,C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, S(O)₂—C₁-C₆-alkyl; phenyl, phenoxyand five- to ten-membered heterocycle and heteroaryl; wherein theheterocycle or heteroaryl contains one, two or three heteroatomsselected from N, O and S; and wherein the phenyl, phenoxy, heterocycleand heteroaryl groups are unsubstituted or substituted with 1, 2, 3, 4or 5 substituents Q^(311c) selected from the group consisting ofhalogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, andC₁-C₄-halogenalkoxy.
 34. A method for combating phytopathogenic fungicomprising treating the fungi or the materials, plants, the soil orseeds to be protected against fungal attack with the composition ofclaim
 27. 35. A seed coated with the composition of claim 27 in anamount of 0.1 to 10 kg per 100 kg of seed.